Buy Now vs. Wait and the Best First Rental for Beginners

17 Sep 2025 · 37 min · 15 chapters

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In short

Whether to buy a rental now vs wait (using 2025 logic), what rehab level is appropriate for first-time investors, unrealistic “zero money/100% financing” expectations, and how to underwrite a flip using annualized return/velocity.

Guests

Dave Meyer (head of real estate investing at BiggerPockets) and James Daynard (on-the-market co-host; Seattle-based investor/operator).

Key claims

Buy now if the alternative is losing time and rent savings; waiting only helps if your saved cash can earn a higher return than the deal’s benefits. For first rentals, cosmetic rehab is usually best; avoid structural “moving walls.” Don’t chase guru promises of 100% financing/no experience—start by earning experience, partnering, or taking a smaller “bite.” For flips, underwriting should focus on annualized cash-on-cash return, not just profit.

Notable examples

Seattle house-hack math comparing $2,000 rent vs ~$1,000/month out-of-pocket with FHA/PMI; and flipping example contrasting a 90-day cosmetic flip vs a 1-year heavy fixer with similar total return.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Buy Now vs. Wait: An Overview

0:00 to 0:30

Exploration of the decision to buy a rental property now or wait.

“Should you buy a rental property now or wait until you've saved up more money?”

Understanding the Questions

0:45 to 1:29

Overview of listener questions related to real estate investing.

“All of the success I feel like is hidden in those specifics on these individual circumstances.”

First Question: Buy Now or Save More?

1:29 to 3:17

Discussion of a listener's dilemma about buying a rental property now or saving for a larger down payment.

“We'll be talking about what's driving the insane, unrealistic expectations out there for many people in the real estate game.”

Explaining PMI and Its Impact

3:17 to 6:33

Clarification of PMI and its financial implications for buyers.

“So James Daynard, who's also in Seattle, tell us how you think through this kind of question.”

House Hacking Explained

6:33 to 10:34

Advantages and strategies for house hacking as a first-time investor.

“own an asset and you have the opportunity, if rents go up, to increase your cash flow and pay out of pocket even less.”

Choosing the Right Property Type

10:34 to 13:39

Advice on selecting between single-family, duplex, and properties needing rehab.

“And if you go over, you're just doing a lot of work and you're not getting cash flow to probably be at the same numbers as a cosmetic renovation.”

Cosmetic Rehab vs. Significant Work

13:39 to 14:01

Discussion on the pros and cons of cosmetic rehab for new investors.

“I think people can go a little bit further than that.”

Navigating First-Time Investment Challenges

14:01 to 16:01

Learn about manageable investment strategies for first-time real estate investors.

“James, you quickly got into that, but I think, you know, just the surface level stuff is manageable for any first-time investor.”

Navigating First-Time Investment Challenges

16:04 to 17:08

Learn about manageable investment strategies for first-time real estate investors.

“AVEN accounts are arranged by AVEN Financial Inc.”

Navigating First-Time Investment Challenges

18:28 to 18:55

Learn about manageable investment strategies for first-time real estate investors.

“Listening to this podcast instead of doom scrolling, smart move.”
Show all 15 chapters

Addressing Unrealistic Expectations in Real Estate

18:55 to 20:07

Discuss the challenges faced by new investors with unrealistic financing expectations.

“answering listener community member questions.”

The Importance of Experience and Realistic Goals

20:07 to 27:38

Understand the necessity of gaining experience and setting realistic investment goals.

“You know, gurus, they're selling a dream, right?”

Upcoming Question Teaser

27:38 to 28:29

A brief mention of an exciting question coming up in the discussion.

“That's the awesome thing about real estate investing.”

Upcoming Question Teaser

29:09 to 30:17

A brief mention of an exciting question coming up in the discussion.

“If I had to hire someone to join the BiggerPockets team, I wouldn't just be looking for someone who checks a few boxes on a resume.”

Flipping Insights with James Daynard

31:48 to 40:00

Gain valuable insights on evaluating flip opportunities and enhancing investment strategies.

“Welcome back to the BiggerPockets podcast here with James Daynard answering your questions, questions from the BiggerPockets community.”
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Transcript

Automatic transcript. May contain errors.

0:00Should you buy a rental property now or wait until you've saved up more money? Buy now and if prices rise and interest rates drop, you'll get appreciation and beat the competition. Wait and you could put down more and have bigger cash flow and be in a relatively stronger financial position. If we had just enough money for a down payment and we were starting from scratch, this is what we'd do right now in 2025.

0:30Hey, everyone. I'm Dave Meyer, head of real estate investing at BiggerPockets. And today on the show, I'm joined by my friend and on the market co-host, James Daynard. James, thanks for being here. I'm excited. This is my favorite kind of show. There's so many things that get popped around. I just love digging into like the little specifics. All of the success I feel like is hidden in those specifics on these individual circumstances. And the cool thing about this is that we have great questions today that even if they don't apply perfectly to your situation. Going through the thought process and hearing sort of the different criteria, the metrics, the thought process that James and I have in answering these questions, I think will help you understand how to drive your own portfolio forward better.

1:12And the questions we have today are awesome and are probably applicable to almost everyone listening out there. First question we have is from an investor who's debating whether to buy a deal now or save up more cash. We're also going to talk about how much rehab is too much rehab for a first-time investor. James, that's right up your alley. We'll be talking about what's driving the insane, unrealistic expectations out there for many people in the real estate game. And we have a couple more questions about flipping houses as well. James, you ready? Oh, I'm always ready. So the first question, I like this because it's from someone named James in Seattle, just like you, but this is a different James, also in Seattle though, who says, I'm looking to purchase my first property for a house hack.

2:00Realistically, I could save up about $25 ,000 by the time my current apartment lease is up next year. That sum is not enough for a conventional loan. So I'd have to take out an FHA loan with PMI and a higher rate if I decide to buy next year. The alternative is I save up for a larger down payment and use a conventional loan. Part of me just says, get started faster. So you stop paying rent and start paying for an asset. And then the other part of me says, waiting and having a bigger down payment will give you more cash flow, both in the short term and the long term. So there's a lot of math that goes into this and I'm having difficulty weighing the pros and cons.

2:40I guess I should explain what PMI is. If you put less than 20 % down on an FHA loan, you'll have something called PMI, which is private mortgage insurance, which is basically just another fee on top of your principal and interest that you're normally paying because the lender is essentially taking on more risk on you because you're only putting 3.5 or 5 % down. And so they charge you for that in monthly payment. And it just adds more expense. So it does hurt your cash flow. But the benefit is that you get to put three and a half or 5 % down to control an asset. I think it's a question almost every investor has asked themselves at one point or another.

3:17So James Daynard, who's also in Seattle, tell us how you think through this kind of question. You know, I love the house hack strategy. My first property was a house hack condo. I moved into it, was able to cut my rent down over like 60 % on my mortgage at that time. People get so confused about the strategy though sometimes because there's so many different opinions. And the purpose of the house hack is to get you into ownership so you own the asset, but also to make sure that you're growing, whether it's you owning or saving money every month. And I think the first step always is, what's your monthly payment on rent?

3:52What can you go buy a property with$25 ,000 down? Where do you want it to be? And can you qualify in those areas? And then you have to look at that variance between the rent and what your monthly payment is. Yeah, that's just the right way to think about this. I get what you're asking is like, what is my cash flow going to be in the future? What is my PMI? But I think the math that James, who asked this question, was alluding to said there's a lot of math trying to think it out. I think James just nailed it on the head. Like, how much money are you going to save? how much better is your run rate, your savings rate in a given month going to be if you keep renting or if you house hack?

4:30Because even paying PMI, right? Like you still might have a financial benefit. And I think that's important. Don't get trapped on cost because cost, it's just a cost of the deal, right? If it gets you into a better financial situation in two years, who cares if you're paying PMI? Who cares if you're paying any expense, like hard money, I pay a lot in interest because it gets me into the deals I need. And I think that's where people get really stalled up. But you have to kind of audit like, hey, what is my goal in two to three years? It's always that question that jams everyone up. Should I wait and put more money down to get the cash flow up?

5:05Should I wait and wait for the market to drop? And then what happens is you wait too long. And the savings account just doesn't earn what you need it to do. And the only time I'm an advocate of waiting is if you can take that$25 ,000 and invest it and make, you know, then like a 8%, 9%, 10 % return higher than you can make on the savings every month. And, you know, I think people just get so jammed up and it really just comes down to cost. And if it's not, take that$25 ,000 and you can still go buy another piece of real estate or invest with someone else and still get into real estate and maybe you rent.

5:40There's nothing wrong with renting. Agreed. You know, I've owned almost every house of mine, except for when I was in California, I rented for three years. I agree with you. I rented for five years recently. When I moved to Seattle, I thought about renting for a while too. Just whatever makes more sense. I'm open to it. Let's just use some real numbers because maybe an example here would benefit. Let's just say your rent, the Seattle, pretty expensive. Let's just assume you have a one bedroom. It's probably two grand here. Seattle's an expensive market. If you could house hack, and even with PMI, you're only coming out of pocket$1 ,000 a month.

6:19That's$1 ,000 in post-tax saving that you are getting, which$12 ,000 a year. To me, I don't know your personal financial situation, but that seems worth it to me. You're just saving now$12 ,000 more while you are starting to pay down your mortgage and you own an asset and you have the opportunity, if rents go up, to increase your cash flow and pay out of pocket even less. That, to me, even if you're paying PMI, makes sense to me. If, for example, though, you were paying$2 ,000 a month in rent and you did the FHA loan and PMI and now you're coming out of pocket$1 ,800 a month, then I don't know if it's worth it.

7:02Like at that point, it's like, oh, 200 bucks a month to take on an asset, the work, there is some risk in it. You know, then it's not worth it. But like if you're meaningfully changing your lifestyle and able to all of a sudden save up significantly more money than you were before, I don't care if you're paying PMI. I think most people who get into house hacking in the first place pay PMI. I think that's the most common example is people do an FHA loan. And so for me, like James said, I wouldn't get caught up on that cost. I would just think, is this benefiting me at the end of the day? And this is why it's so important for people to write down what their goals are in one, three, and five years.

7:42Because if you have goals and you're pushing yourself and they're a little bit higher, that's where maybe you will be more inconvenienced. And that's important because in Seattle, rent can be expensive, but you can go further outside the city, live a little bit further out and get some bigger homes to where maybe you can house hack and rent out three to four bedrooms. And then you will cash flow. Yeah. But it comes with the inconvenience. And that's really what I think a lot of people forget. It's like the owner occupied flip, the house hack. Those are inconvenient processes. You might not have a house for a little while.

8:17You might have some roommates and rent them out. You might have some rotating people, some extra dirty dishes, but is the pain worth it to you? And so, you know, I always encourage people don't listen to what everyone else is doing. Listen to their strategy, write down your goals and then match the strategy with your goals. Not just because Dave's doing or I'm doing it. It needs to match up with your lifestyle. So great question. I think this comes up a lot, but I think you just do the math, right? Figure out how much it will save you or what you would do if you would wait and compare those two things.

8:46I wouldn't think so much about the PMI. If doing it now is going to save you more money, go ahead and buy that deal right now. Yep. All right. Great question. And thank you. Both James is from Seattle. Our second question also comes from Seattle. We picked regional ones for you here, James, but these are applicable to any market and anyone. But just because James and I both live in Seattle, I picked some from local investors here from BiggerPockets. So the question here comes from a guy named Graham on the BiggerPockets forums who said, I finally decided to get serious about investing and wanted to get your perspectives for a first timer.

9:20I'm leaning towards purchasing a single family or duplex for less than$200 ,000. Should I look into a one, move-in ready unit, two, a unit that needs cosmetic rehab, or a unit that needs significant work? With my budget, there may be units that fit the bottom two criteria, but is cosmetic or significant rehab too much to bite off for a first timer? Appreciate any advice if you were in my shoes and had to do it over. Let's just like hone in on the core of this question, which is if you are starting out, almost regardless of budget, do you try and buy move-in ready unit, a unit that needs cosmetic rehab or a unit that needs significant work?

10:03This is a first timer. How would you approach it if you were doing it again? You know, I'm a big value add person, but you don't have to go heavy, right? When I first started buying properties, you know, I started with condos that were really beat up. They're kind of hoarder style condos. And so they were simple because I could get them trashed out, do the carpet, do the paint, do the countertops, do the appliances. I think if you're a new investor and you don't have a construction background, go with the cosmetic because the significant rehab, there's going to be so many mistakes that we make on these big projects that are going to slow down the time, which is going to be a loss of income on a month.

10:38And if you go over, you're just doing a lot of work and you're not getting cash flow to probably be at the same numbers as a cosmetic renovation. And so, you know, I'm a firm believer that you don't want to go too deep. People make this mistake all the time because they're working on a budget and they just buy the cheapest thing they can find. That's not always a good thing. No, you're going to pay more in the long term. And you're going to learn a lot. If you want to go to school, then, hey, it's education and investment. But, you know, starting steps. And one thing on this question that is jumping out to me is, do I purchase a single family or duplex?

11:13It depends on the opportunities in the market. I would say three years ago, single family, that would be what I'd be looking for because multifamily was in a lot higher demand because rates were lower. Now with the current market trends, two to four units, they're not selling as well as single family. And so there's a lot more opportunity. And also when you're trying to buy a rental, when the rental property is in the middle, where it's a cosmetic fixer, their rents are typically not as high too, because they're like average. You can make that property a prime property or a premium property in your market for low amount of cost and get a high kick on your rents.

11:48And so like, if I'm looking for anything right now, and I was a first time investor, house hacker, you know, get going on my investing, I'd be looking two to four units because there's the lowest amount of demand. And when you're buying in the area with the lowest amount of demand, you get the best possible deal. Yeah, I'm 100 % with you on this one. I think, you know, for probably 80, 90 % of new investors, the cosmetic rehab is the best first deal. You could buy an existing unit if you want, but you're probably not going to get the same level of cash flow and you're not going to learn as much.

12:18And I buy some stabilized units, but my first deal, I did cosmetic rehabs. And you know what? I learned plenty. I didn't need to, I was still messing up on a cosmetic rehab, you know, like I didn't need to do a heavy value add to go to school. At least for me, I was had no construction background and even just doing simple stuff like a bathroom reno or painting or resurfacing a driveway. Like I had never done any of those things and it was stuff that still I learned, but it was a manageable amount of learning that like I could take on at an appropriate pace. I didn't have to do it all really quickly.

12:59I was already getting rents. I could do these things, you know, stagger them one at a time so I could build out my network of contractors. I could do research on what I should be paying for these things and the best ways to go about them. And to me, that was like the right blend of getting the right return and learning at an appropriate pace. So it wasn't so overwhelming that I was getting discouraged and panicking and having to spend tons of money. But I was, you know, eating some humble pie about what I knew and was getting an education in real estate at an appropriate pace to set me up for a career in real estate.

13:36So for me, I think those are always the best. What that means, some people call paint cosmetic. I think people can go a little bit further than that. I think, you know, paints, floors, I think even kitchen, bathroom rentals, like those things I think are manageable for a first-time investor. It's really like the structural stuff that honestly, I've avoided pretty much all of my career because I just, I don't want to mess with that. James, you quickly got into that, but I think, you know, just the surface level stuff is manageable for any first-time investor. Yeah. Stay away from moving walls. Yeah.

14:12That's where cost compound. And if you don't, you don't know what you don't know. It's easier to negotiate a flooring installer than an electrician and a framer because you're moving walls around. That's a lot more complex and definitely take your steps. I mean, I made the mistake of, hey, I did a couple flips, bought a couple of rentals that were condos. I had massive success. I was like, I'm Superman. Then I went and bought a huge fixture and I got my clock cleaned in 2008. Best education I ever got. Great question. I love this question and I love it so much because I think it has a concrete answer.

14:45There are so many questions in real estate. It's like, oh, it depends on this and your goal on this. But I think for most people, like cosmetic fixer is the right answer for their first deal. So I'm glad we can give such a clean response to this one. We have more questions coming up right after this quick break. So stick with us. Most banks will give you a line on your primary residence and stop there. Avon looks to underwrite the equity in your investment property, the second home you have, the property you hold in your own name, and put a line of credit against it on a visa card. Same asset, same logic.

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18:54Welcome back to the BiggerPockets podcast here with James Daynard answering listener community member questions. before we talked about saving up or buying now. We also talked about the right level of rehab or condition of a property to buy for a first-time investor. Next up, we have a question. It's kind of just more of a comment I wanted your take on, James. From Charlene in Virginia Beach. She said, sorry, but let me rant for a minute. I've been talking to a lot of people lately who want to break into real estate with zero experience. Most of them just took a class from some random guru and now expect 100 % financing on the purchase and 100 % on the rehab.

19:37Then when I give them a realistic number, they call me a scammer. Honestly, it's frustrating and it feels like a waste of time. For context, I manage an assisted living facility, broker money, and also do fix and flips. I've been in real estate for quite a while and know firsthand it's not easy. The business takes skin in the game, experience, and realistic expectation. What's going on with this mindset? What do you all think is driving this trend? There's a lot in here, James. I think you and I share some of the same thoughts about this, but take it away. Let me know what you think. You know, gurus, they're selling a dream, right?

20:14And the thing is, it is a dream that you have to put together when you don't come from a lot of money. And I mean, I got started in real estate and I didn't have a lot of money. I was working at Red Robin and I was saving tips and I was saving everything I could, but they didn't mean I had enough money to buy a house. And, you know, and so I kind of took the service approach of going and wholesaling, working with some investors, building the relationship, and they funded me the deal. But, you know, everyone wants the dream and they think it's easy because someone's talking about it and it's not.

20:46And, you know, for people out there, you can work with someone to borrow money. You can get a hard money loan for 85%, 80%. You can borrow a second. You can partner with somebody. Those are realistic investment platforms. Those are not unrealistic. What is unrealistic is if you're new and you don't have any experience and you don't want to put in the work to start building the experience to just go expect to go get all this money. You have to put in the work no matter what. And that's what people are doing is they're skipping the work. You know, like if I have a contractor that doesn't have any money and he's never invested before, but he came to me with a good deal and a plan to fix the house.

21:25That's a good opportunity to get 100 % financing with somebody or a partner. But if you're new, don't focus on getting the deal and the money. Get the experience. That will attract better things. I couldn't agree more. I think there's a lot here. First and foremost, it is social media. A lot of people sell unrealistic dreams. I think that is just at part of the core of this, is there are a lot of folks out there who are saying, you can do this, low money down, no experience. All you got to do is go out there and call a million lenders or call a million banks. Like, I'm sorry. It's just, it doesn't work that way.

22:01Actually, James, at one of the walkthroughs you and I did together here in James, there's a young guy who came up to me because I do some private lending, seemed like a really smart, interesting, hardworking guy. And he was like, I don't have a lot of experience. Like what would I have to do to get you to lend to me on a flip? I was like, there's literally nothing you could do. I wouldn't do it. Like there it's true. Like you have no money and no experience. Like I'm not going to do it. So I was like, what you have to do is like, go find a way to be a partner on a deal. Go get 5 % of a deal, go get 10 % of a deal, go work for James or someone else who has experience as a PM, like, or save up money.

22:40But like, if you're coming to me and saying, I have no scale and no money, like what I could lend to anyone. I could lend to an experienced flipper. I could lend to someone who has money, who just needs help with cashflow management. Like, why would I choose you over everyone else? The answer is I'm not going to. And so like, I just think that expectation needs to be set. You can start with no money and no experience, but you have to take off a bite-sized chunk. You can't have it all when you have nothing to contribute. And I'm sorry that I know a lot of people say out there It's just hustle and effort.

23:15That is true, but that hustle and effort needs to be extended for a realistic timeline. It needs to be over a year or two years or three years before you're going to get someone to actually commit to you. If you think that you're going to walk in with nothing but your own attitude and get someone to part with hundreds of thousands of dollars, I'm sorry, but you're insane. That's just not going to happen. Yeah. I mean, my own little rant right now is, you know, one thing is their social media and other platforms and conferences, they're really good, right? You can learn a lot, but also they can be a little bit bad.

23:49You know, I have seen a lot of newer investors get access to capital because they start raising it, right? Because they're promoting their deals. And I think that's great. Capital is the engine for growth, but don't abuse it either. Holy smokes. Like the one thing I've learned in my life is don't abuse debt because no matter what, debt will roll you if you don't use it correctly and you don't need to be greedy. Yep. You know, for those who are new though, because that's a frustrating thing to hear, there always is a way, you know, go find someone in the market. Like Dave said, go work for them.

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24:19You know, you can make money that way. I do believe finding a deal creates a lot of value and you don't need a lot of experience to do that sometimes. Sometimes when you're new, you just stumble into a home run deal. And, you know, like what I do with a lot of wholesalers, too, that bring me deals and they want to get involved in flipping. They don't have a lot of money. Forfeit your assignment fee. Like if a wholesaler brings me a deal and I say they're going to make 20 grand on this house and I got to come up with 100 to buy it. I will let the wholesaler defer their assignment fee and take that cash and invest into the deal with me.

24:51And so I do that to kind of help people grow. But, you know, if you're new, find someone local in your market that you can work and offer services to and help. and learn how you can start building a career. It doesn't really matter if you're talking to some guru online is in Florida and you're in Seattle. They're going to give you concepts, but they're not going to give you resources. So go find the person in your market with resources that can really help develop you as you help them with their business. Yeah. It takes a little bit of humility. Imagine in any other industry, if you just walked up to an experienced CEO and it's like, I want your job.

25:26It's like, I want to have the same job as you. You would get laughed out of the room, right? Like you have to sort of, you have to earn your way in. You got to like pay your dues in this industry unless you come from money or have experience from another job. Like you're a contractor and want to get into this. Like you have to learn. And so I totally agree. I think there's like essential to being successful in real estate investing is having appropriate expectations. and I just disagree with this idea that you're like, oh, if you set your goal super high, then you're going to achieve it. I actually think it's kind of the opposite.

26:04I think you need to like have realistic goals that you can just make incremental progress towards. Because if you say like, oh, I'm gonna make a hundred grand next year as a wholesaler and you have no experience, like it's just not gonna happen. You're gonna get discouraged and then you're gonna quit. Whereas instead, if you said like, my goal is just to get piece of one deal. That's all I want is to get a piece of one deal. That's achievable. Go do that. And then the next one, get a bigger piece of your next deal. That's achievable. And then maybe your goal is by two years from now, I want to own my own property outright.

26:38That's achievable. Like set achievable goals and you can build off that. You can build momentum. Whereas if you set these unrealistic expectations, you're just going to fail. And like that sucks. And I know people on social media like to promote these ideas and get people hyped up on it. But it's just, it's doing you a disservice. So, you know, that's my rant. I mean, the reality is, you guys, this is not an overnight success. I knocked doors for 10 months and didn't make a dollar. And the people's problem quit too early. Then I started finding the deals. Then I would sell deals to investors. I started building the relationship.

27:11That's how I got my 100 % financing on my first flip. It was by not quitting, providing value, selling people deals, and then asking for help after I built the relationship with them. That's how I got money on my first deal. We're talking like 18 months into my career, 15 months of my career. It's not tomorrow. And I had to provide value. I mean, people just expect too much now. Like, go earn it. Yes, exactly. Go earn it. It's a job. It's a business. Go run a business. Do your job. You can succeed. That's the awesome thing about real estate investing. It's like, if you stick with it, it's not rocket science.

27:44You can succeed. You just need to put in the effort. We do have one more great question, James. This one is right up your alley. I'm excited to hear your answer to it. but we have to take one more quick break. We'll be right back. Tax season reminder for all the real estate investors listening. If you own rental properties, short-term rentals, commercial buildings, basically anything that's not your primary residence, you need to know about cost segregation. It's an IRS compliant strategy that lets you accelerate depreciation on your properties, which means you're paying less in taxes this year and keeping more cash in your pocket for your next deal.

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31:48Welcome back to the BiggerPockets podcast here with James Daynard answering your questions, questions from the BiggerPockets community. One more question for you, James. It comes from Liam in Denver who says, Hey, everyone. I wanted to get some insight on what you look at when running the numbers on a flip opportunity. James, this is your wheelhouse. But Liam said, past your standard ARV rehab costs, desire profit, and max purchase price, what questions do you like to answer? Do you look by neighborhood, speed of sale, average home costs, and layouts? Is there anything out of the ordinary that you have found useful?

32:24And James, I'm going to let you one take this away because I am going to be writing down notes. I'm doing my first flip right now. And I'm going to be just going to the school of James Dannard right now. You know, this is actually probably my favorite question I could have got because like, I only got this clarity like four years ago, five years ago when I was flipping homes. I always looked like, hey, if I buy it, you look at the Performa and we all get distracted by this shiny estimated net profit number. We were like, look how big that number is. And I think one of the biggest mistakes is people just look at profit.

32:57and one of the best pivots I ever made was about five years ago. I switched to annualized return because it told me whether it was a good deal or not. Right. So I love that. It is all about velocity, money, and cash, especially in flipping is a high risk business. But so the concept behind that is if I go buy a home run deal, you know, I got to put a hundred thousand dollars up and I'm going to make a hundred thousand dollars. That's a hundred percent return home run, but it's going going to take me a year to complete. That means I'm making 100 % return in 12 months. Great return, no problems with that.

33:30But that's going to come with some hair too. A lot of hard work, usually a lot more management. I got to visit the site a lot. It's a heavier fixer. If I can go buy a cosmetic fixer and be in and out of a deal in 90 days, and I got to put up 100 grand and I'm going to make 25 ,000, I can do that four times in a year, which gets me to the exact same return as this big fixer, but probably substantially less work. And so that's why we always look at annualized return. You know, the annualized return is how much cash am I putting in? How much cash am I getting back? And then how quickly am I doing that?

34:03And then look at it on an annualized basis. And that's our metric for buying. We don't buy on profit. We want to buy at a 35 % cash on cash return in six months. 35%. Okay. That is my goal. I love this because I I actually, I think it sort of equalizes flipping to other investments as well. Because a lot of times you hear these huge numbers in flipping. You're like, oh, I made 60 grand. It's like, that's a lot of money. But did you invest 300 grand? And was it a super high risk project? Because that's very different than investing 100 grand into a cosmetic flip. You know, like it's very different.

34:40So I like that idea of annualizing because it allows you to sort of compare apples to apples. But the part of it I still struggle with is the risk part. So like you're good at this, right? So you can look at a deal and sort of back to Liam's question, like you can look at ARV, you can look at comps, you can look at your reno budget and feel pretty good about hitting that 35%. But like it's different for someone like me to go out and say, I want to target a 30 % annualized return, but I'm not as good as the inputs. Like my assumptions about what it's going to cost, how long it's going to take, how quickly it's going to sell, what it's going to sell for are not as good.

35:20And so like, how do you sort of work on and improve your assumptions about the deal to make sure that the deal does have a very high chance of hitting that 35 % cash on cash return? Well, you know, I think the first thing is you don't need to buy your first deal on your own, like investing with an operator. so you can watch the numbers go down, the construction, the delays, the issues, how they underwrite the property. That's the first thing, is invest in someone that knows what they're doing because you get to cheat and watch the process. The next thing is you have to build the right team around you.

35:56One of the biggest mistakes flippers make is they go chase the deal first. And they're going, I need to find the deal back. You don't even know what a deal is if you don't have the right team around you. I'm sorry. Like everything you're looking at from the wholesalers you're going off numbers that aren't yours and you're looking at it wrong. And so it's all about building that team, you know, like the bigger pockets agent finder, right? You can find, you want to find the specialist, narrow your ARV. That's the first risk you need to do. What is this thing worth? How long is this going to take to sell?

36:26And what is the current market conditions to judge risk, right? If I know what it's worth, I want at least three to five data points that are going to tell me that that's worth all within a local market. If I don't have those data points, I have to assume the worst. The next is what's the days on market and how long does it take to sell? That is going to tell you your annualized return. Like if I look at comps and it goes, it takes 30 days to sell here. Then it takes 30 days to close. That's 60 days. Then I have to lean on my next partner, which is the contractor and go, how long is this going to take to renovate this scope of work?

36:59And the longer you're in a deal, the more risk there is. and so you know you but you can narrow those risks by having a good contractor that you can depend on on pricing and how long and then a broker they can not only just explain the value but they have to be explaining the full picture this is going to take some time to sell and if it's going to take longer the market's slowing down then you have to buy deeper and you have to get a better return and so it's really about building that team around but i i really do believe there's nothing wrong with part like i'm doing a couple deals with some operators right now because I don't know much about, like, I like the investment.

37:34I've never done it myself, or I have. I just kinked the system too much. And so I'm letting this operator do it. So I get to watch his process all the way through too. That is some of the best learning you can do is watch someone run into hiccups and then have to pivot off. Yeah, and I guess the thing I'm trying to do, at least as I'm exploring flipping and just trying to help Liam, it's like just trying to get reps. Like I, you know, I am, I have closed on and I'm starting to work on my first flip, I'm probably not realistically going to buy another flip while I'm doing this first one, just trying to take it slow.

38:10But like, I'm still looking at deals and starting to run numbers and just getting practice at that. Like just even considering, you know, scoping out, writing up scopes of work at looking into comps and just getting reps because I've done this for years on rental properties and I can run the numbers on a rental property in like 10 minutes, you know, like it doesn't take a lot of time. flipping for me, I'm still struggling to like, feel confident in my numbers. But like, that just takes practice and experience. And I think like, the more you can do it, even if it's not on a real deal, the better that you're going to get at it.

38:42So that when you do find a deal that you're are going to execute on, you'll you could do it with confidence, because you've like done the process, you've like built the muscle of running these deals long enough that you will feel confident of that. Well, and one thing I think is great education for anybody. It's like, even when you buy your first deal, it's like a lot of times people just look for that one contractor. They put them on it, go get three estimates. Even if you have the guy and he hits the number the first time, get three estimates because you get to look at these proposals, the pricing, how it's broken down.

39:14And then sometimes I'll get two different types of estimates just to see, well, if I wanted to do this much work on it, how much will it cost? And the more you can educate yourself on the middle side, that's really where you can feel a lot more confident, right? The reason I'm confident is I bought a lot of houses and I've made a ton. I probably made more mistakes flipping a house than anyone in the nation. You know what? I honestly believe that, but you've also probably successfully flipped more houses than anyone in the nation. Yeah. Cause just, you have to fail to succeed, right? And you're going to run into problems for sure.

39:44And so when you do that first deal, don't just prep it and go take numerous swings on that deal. So you educate yourself. You can really maximize your experience on that first one. All right. Well, James, thank you so much. I knew this one would be right in your wheelhouse. Thanks for answering this one and for joining us for answering all of the BiggerPockets community questions here today. I will come back anytime. BP Con's coming up, guys. If anyone sees me in the halls, Dave will attest, I'll just sit there and answer questions for hours. You should not be advertising that because he will.

40:14But don't be greedy with your time, you guys. Go out to the conference. If you have questions, ask those questions and talk to people that care. You're right. And it's your opportunity to get some clarity and move on. I honestly, even though I'll talk for like eight hours, I'm so fired up by the time I'm done. Oh, it's the most fun. I look for, it's like my favorite weekend of the year. I love going. It's so much fun. And it's less than a month away, like three weeks away. I'm so stoked. Yeah, it's gonna be a good time. There are still tickets, by the way, if you wanna go biggerpockets.com slash conference.

40:42You can also hit me up. I have a discount code if anyone is interested. you can find me on Instagram at the data deli and I'll pass that along, or I'm sure James has one too, if you want to connect with him. Thanks again, man. And thank you all so much for listening to this episode of the bigger pockets podcast. We'll see you next time. Athletic brewing company crafts award-winning non-alcoholic beers for those who want to be part of every round with over 185 flavor awards. They're exceptional NA beers that fit your lifestyle and any social occasion. Summer's full of good times and athletic fits right in.

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From the publisher

Should you buy a rental property now or wait? If you buy now and prices rise, you’ll get all the appreciation that comes with it and have the chance to refinance at any point in the future. But waiting to have a larger down payment could get you a better loan and put you in a stronger financial position. You want to get into real estate investing soon, so what should you do?

We’re answering this question, and more, on this Q&A episode where we field actual investor dilemmas and share what we’d do in these situations. First, the classic buy now or wait debate. Mortgage rates are falling, and so are prices in many areas, and if you’ve got just enough money to buy your first rental, is now the time to do it? Or, do you wait and save, bringing even more money to the table?

Should you renovate a house as a first-time real estate investor? If done right, the benefits could be massive, but veteran house flipper James Dainard says there’s only so far into a renovation you should go as a beginner. Plus, do you want 100% financing as a new investor with no experience? We’ve got some interesting news for you! Finally, the one flipping metric to rule them all—what James uses on every flip to see if it’s worth it. 

See Dave and James live at BPCON2025. Limited tickets are still available!

In This Episode We Cover

Whether to buy a rental property now or wait until you have more saved up (is it worth it?)

Should you buy a move-in-ready rental property or renovate as a beginner?

Can new investors really get 100% financing on their first real estate deal?

Why James stopped looking at “profit” before deciding on whether a flip is worth it 

How to get James’ personal advice on your next deal (you have to bring him this) 

And So Much More!

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Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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