This “Hybrid” Rental Strategy Is a No-Brainer for Rookies in 2026 (Rookie Reply)

27 Feb 2026 · 26 min · 6 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Real Estate Rookie Podcast Episode Notes

Episode Overview

  • Title: This “Hybrid” Rental Strategy Is a No-Brainer for Rookies in 2026 (Rookie Reply)
  • Hosts: Ashley Kehr and Tony J. Robinson
  • Description: The hosts discuss a beginner-friendly strategy for real estate investing that combines cash flow, appreciation, loan paydown, and tax benefits. They also answer questions from the BiggerPockets Forums regarding rookie concerns and strategies.

---

Key Topics Covered

  1. Beginner-Friendly Investment Strategy
  2. Hybrid Rental Strategy:
  3. Combines elements of house hacking, flipping, and the BRRRR (Buy, Rehab, Rent, Refinance, Repeat) strategy.
  4. Suggested approach:
  5. Buy a single-family home with extra rooms and rent them out.
  6. Live in the property while renting out other rooms for two years.
  7. After two years, move out and rent the property, then sell it after five years for a tax-free gain.
  8. Use the cash flow to pay down the mortgage and reinvest in additional properties.
  1. Buying in Cash vs. Getting a Mortgage
  2. Pros and Cons of Paying Cash:
  3. Paying cash can eliminate debt and associated risks.
  4. However, leveraging through a mortgage often yields better returns since it allows for purchasing multiple properties.
  5. Recommendation:
  6. Consider a cash purchase for value add opportunities where renovation increases property value.
  1. Investing in D-Class Neighborhoods
  2. Opportunities and Risks:
  3. Investing in lower-class neighborhoods can be risky but also rewarding with the right management.
  4. Individual experiences vary; some properties in tough neighborhoods can outperform based on management style.
  5. Advice for Investors:
  6. Engage with property management to understand tenant management strategies.
  7. Prepare for potential surprise costs by including reserves in your financial planning.
  1. Addressing Tenant Management Concerns
  2. Handling Difficult Tenants:
  3. Approach property management with a mindset of providing stable housing.
  4. Build rapport with tenants to improve property conditions and tenant behavior.
  5. Legal and Financial Preparedness:
  6. Include reserves in your financial model for unexpected repairs and evictions.
  7. Understand local laws related to tenant eviction and management.

---

Key Takeaways

  • Importance of Action: New investors often hesitate due to fear of making mistakes. Transitioning from research to action is crucial.
  • Tailor Your Strategy: Understand your personal motivations (e.g., reducing living expenses, supplementing income) to tailor your investment strategy effectively.
  • Utilize Resources: Leverage tools like BiggerPockets Market Finder to identify suitable investment markets.
  • Mindset Matters: Approaching property management with a positive and supportive mindset can lead to better tenant relations and property conditions.

---

Conclusion The episode emphasizes the importance of taking actionable steps in real estate investing, the strategic advantages of leveraging financing, and the nuanced approach required for managing properties in diverse neighborhoods. For rookies, it’s not just about financial investment but also about building relationships and understanding the deeper aspects of property management.

---

Resources Mentioned

  • BiggerPockets Market Finder
  • BRRRR Strategy
  • RentReady (for property management)
  • Fundrise Income Fund (investment opportunity)
  • Collective (financial solutions for solopreneurs)

For more resources and information, visit [BiggerPockets.com](https://www.biggerpockets.com).

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

Chapters

Tap a time to open that second in VO

Answering Beginner Questions

0:45 to 6:14

Discussion on taking action in real estate investing and strategies for beginners.

“on flipping properties and the BRRRR strategy, but I've never mustered the courage to enter the market.”

Exploring Out-of-State Investment Opportunities

7:21 to 14:03

Advice on investing out of state and buying rental properties.

“Okay, we're going to shift gears for a minute to cover something important, especially for new landlords.”

Navigating Investor Fears and Tenant Management

17:58 to 20:50

Addressing concerns of first-time investors about dealing with tenants.

“I'm going to be the one finding and managing the deal, and my parents will help with half of the purchase or potentially even more.”

Reputation and Responsibility as a Landlord

20:50 to 25:31

Discussion on the importance of treating tenants with care and the impact on property value.

“And I think, first of all, if you're already freaked out, that you're just going to get more and more stressed if you actually go and purchase a deal like this.”

Legal Challenges in Eviction Processes

25:31 to 28:04

Exploring the complexities of eviction laws and tenant rights in New York.

“And if you go into it with a different mindset, then I think you do have to question whether or not real estate investing is the right path for you.”

Challenges of Eviction in Buffalo

28:04 to 29:21

Learn about the complexities and frustrations of the eviction process in Buffalo.

“Like what can we do to, you know, make this situation like the last.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:01Tony:Every week we see the same thing happen in the forums. New investors are motivated, they're consuming all the content, but they're stuck because they're afraid of making the wrong first move.

0:13Ashley:So today we're answering three real questions from beginners. We're talking about how much money you actually need to start investing, whether you should invest locally or out of state, and how to get over the fear of pulling the trigger on your first deal.

0:32Tony:This is the Real Estate Rookie Podcast. I'm Ashley Kerr.

0:35Ashley:And I'm Tony J. Robinson. And with that, let's get into today's first question. So our first question comes from the BiggerPockets forums and it says, I've spent the last few years doing light research on house hacking, on flipping properties and the BRRRR strategy, but I've never mustered the courage to enter the market. After all of this time, I realized that I just can't wait anymore. I've graduated it from college and wants to try to do something with my first year out of it. I don't want to live a life of mediocrity. Any advice for potential ways to get started now? Well, first kudos to you for realizing that you can't just keep waiting.

1:12Ashley:I think that's probably the first big step is realizing that at a certain point, we have to move out of the information gathering stage and move into the action taking stage. Because if we don't do that, then yeah, days turn to weeks, weeks turn to months, months turns to years, and years turns into never doing it at all. So I think that's the first step is just realizing that it is important to finally take action. But I think the advice that I would start with, and we echo this thought a lot, but my first thing is understanding what your motivation is for investing in real estate. Sounds like you're early in your career, so you just graduated from college.

1:48Ashley:So for you, it's understanding what's important to you right now as someone who's a new working professional. Are you doing this because you want to reduce your living expenses? Okay, then house hacking maybe makes a ton of sense. Are you doing this because you want to quickly supplement the income you're making from your day job? Then maybe something more active like flipping makes more sense. Do you want the long-term appreciation? Then maybe just some buy and hold properties where you're plopping down 20 % once every three to five years. So I think first just understanding what your motivation is and why you want to invest in real estate is where I would start.

2:20Tony:This would be my plan. I would house hack, first of all, but I would actually incorporate house hacking, flipping, and burying into this strategy. If you are just starting out and you're maybe renting and you have the opportunity to house hack, this is what I would do. I would purchase a property and I would do a single family home with extra bedrooms and bathrooms and rent out by the room. Okay. And then I'm going to live in this property for two years, renting out the other rooms. At the end of two years, I'm going to move out and purchase another property. And then I'm going to continue to rent the house out for three more years.

3:00Tony:I'm going to fill my bedroom, rent it out. At the end of five years or before the five-year mark, I'm going to sell the property. So this will satisfy the property has been your primary residence for two of the last five years. and you'll be able to sell it for tax-free gain and not pay any taxes on the profit of this property. And how I would incorporate kind of the BRRRR strategy into this is I would buy a property that needs to be rehabbed. And I would slowly do work on it over the course of the two years that I'm living there. Maybe you don't have a roommate right away or someone else living in the bedrooms because you're renovating part of the room.

3:43Tony:But I would do that strategy. And by renovating it, you're adding value to the property. Over those five years, those tenants are going to pay down your mortgage. You're going to have, hopefully, you're buying in an area that sees some appreciation over five years. And then I would go ahead and cash out. But at the same time, you're already another three years into your next property. So I would just keep recycling this method, property to property. So for five years, you're getting rental income on these properties. Two of the five years, you're getting a house to live in. And then you're getting a big gain tax free.

4:20Tony:So that's what I would do. If I was starting over and no kids, no family, just me, and I was renting and buying my first property, that is the plan that I would do for even like 10 years. Do it for all your 20s and by your 30s. you could rack up quite a bit of money that way.

4:42Ashley:I love that approach, Ash, and you gave something super tactical. I think the only thing that I would change if I were to implement a plan similar to that is that I don't think I'd sell all of them. I feel like I would try and maybe sell one, keep one, sell one, keep one. That way, at the end of that decade, not only do you have these big chunks of cash you've been able to make, but at least you've got some that you've kept for the cash flow. And we, you know, we've interviewed quite a few people who have used this strategy, but Matt Kruger was the most recent. And, you know, I think he did every year for like two years, every two years for like a decade, he did this and, you know, ended up with seven properties or so that were cash flowing really well, all with these really low debts and really low out of pocket expenses.

5:22Ashley:So I think I would probably make that one small tweak. So that way I'd still get some of the upside in the portfolio that I'm building, but couldn't agree with you more that if I were in my early twenties with no kids, no wife, no responsibilities aside for myself, um, I would probably choose to make my life as uncomfortable as possible during that timeframe. Um, so that way my thirties could be significantly more comfortable.

5:43Tony:And I'm not talking about sleeping on the couch. I'm still having a bedroom and an on-suit.

5:49Ashley:You know, we, I, we laugh, but, um, Craig Curlop, who we interviewed, uh, I can't remember the, the episode number, but his first house hack, that's exactly what he did. He slept on the couch and he rented out all of the other rooms in his house. So if you want to get that uncomfortable, you can. And Craig's obviously going to be a really successful real estate investor, so it's worked out for him. But to Ashi's point, you can still have a little bit of comfort if you choose to.

6:10Tony:Before we jump into the next question, let's take a quick break. Getting started as hard enough and having the right tools in place early can save you from a lot of rookie mistakes, especially when it comes to staying organized from day one. We'll be right back.

6:23Ashley:Billion-dollar investors don't typically park their cash in high-yield savings accounts. Instead, they often use one of the premier passive income strategies for institutional investors, private credit. Now, the same passive income strategy is available to investors of all sizes, thanks to the Fundrise Income Fund, which is more than$600 million invested and a 7.97 % distribution rate. With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar asset class in the last few years. Visit fundrise.com slash pockets to invest in the Fundrise Income Fund in just minutes.

7:01Ashley:The fund's total return in 2025 was 8 % and the average annual total return since inception is 7.8%. Past performance does not guarantee future results. Current distribution rate as of 12-31-2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the Income Fund's Perspectus at fundrise.com slash income. This is a paid advertisement. Okay, we're going to shift gears for a minute to cover something important, especially for new landlords. The shows often talk about getting stuck doing everything ourselves and the cost of sweat equity.

7:31Ashley:The key question is simple. Is my time better spent elsewhere? I use a tool that cuts down on a lot of landlord hassles. And the wild part is, it's just$12 a month. It handles rental screenings, rent collection, maintenance requests, and accounting. All in one platform via a mobile app or desktop. It saves me time in tenant communication and keeps me organized for tax season. It's called RentReady, and you can sign up for a six-month plan for just$1 with promo code BP2025. Pro users get it for free because we believe in it. Just sign in through your pro account to get started. RentReady helps ensure on-time rent with auto reminders, keeps communication professional, and lets you post listings to multiple sites.

8:08Ashley:Check it out at rentready.com slash biggerpockets. That's rent, R-E-D-I dot com slash biggerpockets. Most investors spend all their time talking about their high-level returns. But that's not the number that actually matters. What actually matters is what you keep after taxes. And that's where multifamily real estate quietly stands out. With built-in advantages like depreciation, the right deals can generate steady cash flow while reducing the tax drag. BAM Capital structures its multifamily investments around those fundamentals, pairing tax efficiency with disciplined operators and a long-term approach.

8:45Ashley:This isn't about chasing hype or guessing market timing. It's about building durable, tax-aware wealth over time. Learn more at biggerpockets.com slash BAM.

8:54Tony:Okay, welcome back. We have our second question from the BiggerPockets forums. This one says, hello, everyone. I live in LA and I have been saving aggressively to try and buy a house for myself. I've recently decided to start looking into investing in rentals out of state instead. I have$100 ,000 in cash and as of now, thinking of trying to buy a single family rental in cash if possible. looking for some advice, tips on which markets I should be researching, and if it's a good idea to buy my first investment property in cash, or should I consider financing something that would be more turnkey?

9:28Tony:Thanks in advance for all the help and words of encouragement. Finding this community has really got me excited and motivated. Well, first of all, we love to hear that, and welcome to the BiggerPockets community. So$100 ,000 in cash, a great chunk of money to be able to get started in real estate. So advice or tips on markets to research in. You definitely could buy a property in cash in Buffalo, New York, Syracuse, New York. It won't be the best property, but you could definitely get a decent property and then do some rehab and add some value to the property. but those are at least two markets I know of.

10:14Tony:But I think your first step should really be using the BiggerPockets Market Finder. And you basically go through the steps of looking through markets that kind of fit your criteria. It's a really great tool that you can find, biggerpockets.com, right at the top there is the Market Finder.

10:30Ashley:I think my first question, though, is why the feeling that buying in cash is necessary for that first deal? Is it because you just don't want the, maybe the risk associated with getting debt on your first property? Or they mentioned at the end here, or would buying something turnkey make more sense? Maybe the person asking this question is assuming that they're buying like a really rough rehab and that's why they want to buy in cash. So I think just answering that question first would be important. Because mathematically, you're going to get a better return on your investment if you include leverage in the purchase.

11:07Ashley:Because if you've got$100 ,000, you could spend$100 ,000 to buy that property, or you could spend maybe$25 ,000 to get that same property. And obviously, your cash flow will be a little bit less, but your return on that property would be significantly more. So you could go get four properties at$25 ,000 down each or one property in cash at$100 ,000. And in theory, those four properties at$25 ,000 down each would generate more than the one property paid off. So I think just asking yourself or trying to get an understanding of like, why are you focused on the cash perspective? I think for me, if I were paying cash for a property, it would only work for me if it was a value add opportunity, meaning I could buy something, invest the money to renovate it, and then refinance that property and hopefully recoup some of that cash that I put into that deal.

11:57Ashley:And that's what the BRRRR strategy is. So 100K in cash can get you into a lot of markets across the country. Like Ash said, it's going to be maybe smaller markets. But it is an entry point in a lot of places. So I think that's where I would start is if you do want to go cash, look for a value add opportunity where then you can buy it, renovate it, refinance it, rent it, repeat it all over again.

12:20Tony:And another option too, especially like being out of state, it can be more difficult, not impossible and definitely doable to build your own team and have your maintenance guy and your property manager and all the vendors that you need and your boots on the ground, your agent, things like that. But another option, if you don't have a team and you're looking at a market is looking at a brand new build. We're seeing so many builder incentives, like buying down your interest rates, giving you seller credits, upgrading your home appliances, different things like that, where that may be a great option when investing out of, say, If you don't have a team built, you know, a lot of the properties I buy, they're older properties.

13:04Tony:And, you know, sometimes we're not doing a full, complete gut renovation on them. And, you know, you're going to have older plumbing. You're going to have older exteriors, different things where, you know, you need to have a boots on the ground handyman that's going to go in and make those repairs and stuff like that. So maybe looking at a new build in an out-of-state market is also an option for you. So obviously it's going to have to be if you do decide to get financing because I don't know of any new builds unless you're buying maybe a tiny home that's 200 square feet. You could get a new build for$100 ,000.

13:42Ashley:Yeah, the builder incentives, they've been pretty crazy, I think, these past couple of years as builders have fought with climbing interest rates and squeezed budgets of buyers to make sure they can keep moving inventory. So yeah, definitely a unique thing to try and take advantage of, given where we're at right now in the cycle of the market. All right, we're going to take a quick break before our last question. But while we're gone, be sure that you are subscribed to the Real Estate Rookie YouTube channel. You can find us at Real Estate Rookie if you haven't subscribed yet. And we'll be back with more right after this.

14:14Ashley:Billion-dollar investors don't typically park their cash in high-yield savings accounts. Instead, they often use one of the premier passive income strategies for institutional investors, private credit. Now, the same passive income strategy is available to investors of all sizes, thanks to the Fundrise Income Fund, which is more than$600 million invested and a 7.97 % distribution rate. With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar asset class in the last few years. Visit fundrise.com slash pockets to invest in the Fundrise Income Fund in just minutes.

14:52Ashley:The fund's total return in 2025 was 8%, and the average annual total return since inception is 7.8%. Past performance does not guarantee future results. Current distribution rate as of 12-31-2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income fund's prospectus at fundrise.com slash income. This is a paid advertisement. The rise of the tech-savvy investor is here. You don't need a huge team or tons of overhead to manage rental properties. Just the right tools. So I want to tell you about how I use RentReady to get ahead.

15:22Ashley:For landlords who treat their time like capital and recognize the cost of sweat equity, this tool gives you everything you need to scale. Rent collection, tenant screening, maintenance accounting, so that you're organized come tax season and you can run numbers in preparation for future deals. And more, all in one platform via a mobile app or desktop. Modern landlords don't just own property, they optimize it. RentReady will keep you organized, running leaner and ready to grow. Start with RentReady. Visit rentready.com slash biggerpockets. That's rent-r-e-d-i dot com slash biggerpockets. And use code BP2025 to get RentReady's six-month plan for a dollar.

15:58Ashley:Here's the truth about passive investing. If the strategy isn't right on day one, the returns won't save it. Multifamily real estate offers structural advantages many investors are overlooking, including depreciation that can help offset taxable income while cash flow continues. BAM Capital builds its investment with that reality in mind. They are focused on solid operators, tax efficiency, and long-term performance. For investors who want real estate exposure without being landlords and who care about consistency over hype, this is a smarter way to allocate capital. Learn more at biggerpockets.com slash BAM.

16:33Ashley:Passive income sounds amazing until it involves 17 apps and active maintenance. That's where the Gemini credit card comes in. It earns you Bitcoin back on everyday purchases automatically. You use it like a normal credit card for lunch or gas or groceries. And every time you swipe, you earn up to 4 % back instantly in Bitcoin or one of over 50 other cryptos sent straight to your Gemini account. No points to track, no categories to activate, no waiting to redeem rewards. It just shows up and there's no annual fee, which is great because paying money to earn rewards has really never made much sense.

17:07Ashley:So if you've been curious about building your Bitcoin stack without constantly thinking about it, this is one of the simplest ways to start. Go to Gemini.com slash card to learn more. Terms apply. See the link in the description for more information regarding rates and fees. Issued by WebBank. Some exclusions to instant rewards apply. This is not investment advice and trading crypto involves risk. Check Gemini's website for more details on rates and fees. All right, rental property investors, listen up. Our friends at Dominion Financial already have some of the best DSCR rates in the industry.

17:36Ashley:Now, they're the fastest, too. They just launched 10-day DSCR closing. That's right, 10 days. And they're still the only lender with a DSCR price beat guarantee. That means faster closing, the best terms, zero guesswork. That's Dominion Financial. Check them out at biggerpockets.com slash Dominion. Again, that's biggerpockets.com slash Dominion. All right, welcome back. Our final question for the day also comes from the BiggerPockets forums, and it says, I'm a 28-year-old beginning investor, and I've been more than ready intellectually, financially, et cetera, for almost a year now to buy my first property.

18:12Ashley:I'm going to be the one finding and managing the deal, and my parents will help with half of the purchase or potentially even more. The problem is I'm looking at such a low price point in my area that when I actually get up and close to the house and meet the tenants, I get freaked out. How am I going to deal with these people, especially some of the section eight people I meet, even if I outsource to property management, who knows what repairs and other surprises are in store for me in some of these places. Does anyone have experience with this? Would you say you have to approach some like investments as a semi slum Lord, just because that's the reality.

18:47Ashley:Um, so great question. Um, I think the first thing that I'll say is there's definitely truth in the idea that, But we talk about class neighborhoods when it comes to real estate investing that some of the lower class neighborhoods, your C class, your D class, have tenant pools that are a little bit difficult, a little bit more difficult to manage. It doesn't mean, though, that investing in the quote unquote D class neighborhoods is always going to be a bad investment. I think about our friend Steve Rosenberg, and he shared this story on stage a few times and I've heard him speak. but he had this portfolio of single family homes in a D-class neighborhood.

19:26Ashley:And Steve had a lot of experience in property management at that point. And it was the worst part of his portfolio. And he just said, hey, I'm going to bundle these all up and I'm going to try and see if I can sell them off to someone else. And he sold them to a buyer who bought all of those problem properties that he had. And then he ended up seeing that person like a few years later at a conference. He's like, man, hey, how's that portfolio doing? And the guy who bought them was like, man, these are my best performing properties. So same exact homes, same exact neighborhood, same exact tenant pool, but two slightly different approaches in how they manage it.

19:55Ashley:And for one person, it was their worst performing portfolio. For the other person, it was the best part of their portfolio. So I think a lot of it does come down to you as an individual operator and how you manage those tenants. So that's the first piece. The second thing that I'll say is, is that if you're worried about things like additional expenses around repairs or evictions or whatever those surprise costs might be, work those into your underwriting. So maybe you account for the fact that on day one, not only do you want to account for your down payment, your closing costs, whatever, you know, repairs you need to do, but you're also accounting for on day one, maybe six months of reserves.

Read the full transcript

20:31Ashley:So if you have a fully funded six month reserve account on day one, that'll give you some flexibility for whatever issues may or may not arise and allow you to sleep a little bit easier at night. So even if you had to abduct someone on day one, you know, you've got enough money set aside for that specific property to not have to lose sleep. So I think those are the first two big things that come to mind for me, Ash.

20:51Tony:Yeah, those are all great points. And I think, first of all, if you're already freaked out, that you're just going to get more and more stressed if you actually go and purchase a deal like this. But I think one thing is if you do outsource to a property manager, ask their experience handling with different classes of tenants. Do they have properties that are already in a C-class area or B-class area. So getting their understanding of and then asking how they deal with different, you know, things that could happen and how they handle, you know, if a lot of repairs come in or other surprises. So I guess I'm more curious as to what you are freaked out about.

21:36Tony:Is it just how they kept the apartment, that it wasn't kept clean, That is what kept nice. I've had quite a few Section 8 tenants, and all of them have taken very good care of the property because they don't want to lose their housing voucher. I think in Buffalo, it's like an eight-year waiting period to get a housing voucher. So if they don't want to be kicked out because they don't want to lose their housing voucher. And they also have an inspection every single year where the inspection is more for you as a landlord to make sure the apartment is in compliance. So make sure when you're touring these properties and they have Section 8 tenants, make sure that they will pass the Section 8 inspection because that could be the motivation for somebody selling is like, you know what, there's like too much that Section 8 wants me to repair.

22:26Tony:I'm just going to sell the property and be done with it. So if you just contact the local housing authority that actually gives out the Section 8 vouchers, they'll be able to tell you what they look at in an inspection, you know, and like none of it is crazy. Like these things should be done in the property anyways, you know, like any outlet is grounded by, you know, has a GFI outlet by any water source and things like that. But the thing that I will say here is that if you are going to approach this property and you said approach slum-like investments as a semi-slum lord, I would say no. I would say that this is not the right mindset to have going into the property.

23:14I think that you can do things to

23:20Tony:change the value of that property. So for example, we have a tenant that constantly doesn't pay or she pays, but she's late. The place is just packed with stuff. She, you know, doesn't take great care of the property, things like that. But we've done a couple things and it really has changed how she is treated and taking care of the property. So we actually got her a dumpster. We paid for it, got her a dumpster, and she actually filled up the dumpster. Whenever the landscaper would come, he would help her clean up the yard so he could actually mow the grass. And she actually started to feel bad, and she'd run out there when she saw him pulling it and go and clean up the yard and stuff.

24:10Tony:So I think if you have the semi-slumlord mentality, it's just going to keep your tenants in that mindset that you don't care. Why should they care? So I think kind of shifting that mindset can actually go a long way. And I think this is something that's a huge debate. So let me know in the comments, do you think like you should do these extra things for tenants that are living in the property to try and help them out, even though you are running a business and your bottom line is your bottom line and you want to be profitable and you want to make as much cash flow as you can. So let me know in the comments below how you see it and what would you do in situations like this?

24:49Ashley:Well, Ash, kudos to you. I think it is somewhat counterintuitive for a lot of investors to reinvest into a property that they feel isn't being treated well by the tenant. But I think it goes to show that people are still people. And if you can kind of touch them in their hearts or kind of speak to what motivates them, then maybe you can have their behavior change in a way that's beneficial for both of you. But I couldn't agree more that no one should go into real estate investing with the intention of being even a semi-slumbered, right? Like the goal for us should be to provide safe, clean, relatively affordable housing for the people that live in our properties.

25:31Ashley:And if you go into it with a different mindset, then I think you do have to question whether or not real estate investing is the right path for you. But at the end of the day, we're providing people with housing, which is for many people, their biggest expense in life. So we want to make sure that we're doing it in the best way possible.

25:50Tony:Yeah. And I think some of these little expenses you do to help the tenant actually help you out in the long run that your property is being taken care of and you don't have this huge turnover expense when you need to renovate it to get somebody else into it. And I will say, as nice as I sound, I did try to evict her, but she paid rent literally at the courthouse and they dismissed the eviction. So I still am very business minded, but like I was like, OK, I need to find a different way to solve this problem and a different solution. And in New York State, it's very hard to evict someone unless it's for nonpayment.

26:24Tony:And she ended up getting caught up. And it's just the attorney fees start racking up when you keep sending notices and start the eviction process. And then they end up paying before, you know, like I think we've tried to do it like three times with her. And she always does pay. It's just, you know, it's late and late and late. But I think we found a better workaround as to, you know, what can we do to kind of make it the situation, you know, more bearable for both of us. And it definitely has been working.

26:58Ashley:Ash, let me ask one last follow-up question on that. Is there anything in New York law that states if someone has been served in eviction like X number of times that like at some point you can maybe skip the line and just kind of like go to the eviction? Or can it be this kind of game of like cat and mouse forever?

27:18Tony:If anybody knows of that loophole, please tell me because I do not know of it or how to do it because all I know is you got to start the process all over again. I mean, you can't even deny someone in New York State because they have a previous eviction anymore.

27:37Ashley:But could you non-renew their lease for that reason?

27:40Tony:Yep, you could. You could do a non-lease renewal. But then if they don't move out, then you're going through the whole eviction process to get them out for non-renewal, which you can do. It's just you're starting the process over again. And I've tried to do it a couple times. And the judge is always like wants the attorneys to work through it. Like what can we do to, you know, make this situation like the last. Like literally it seems like the last thing they want to do is kick somebody out, which I understand that. But like, my God, every time my attorney comes back and says, OK, so we worked out a payment agreement and we're going to do this payment plan.

28:22Tony:And he's like, they just won't evict. And it's mostly like right in the city of Buffalo where this happens, where like the smaller towns are way easier and more lenient. But in the city of Buffalo, like they constantly want to see like something worked out. And at first it was never like that 10 years ago when I first started investing. But now it's like you're going to court multiple times for this.

28:48Ashley:And so then it's like, is it even worth the headache? Like it's a headache either way.

28:52Tony:I literally at one point my attorney called me. I think it was like his fourth time in court with this one person we were evicting. and he's just like, I'm done. Sell your properties in Buffalo. Why would anyone invest here? And I was like, okay, I'm mad about this, but you are definitely way more mad than me. It was funny. I mean, not funny because it was an awful process.

29:17Ashley:But we can look back and laugh on it now.

29:19Tony:Yeah, yeah. Well, thank you guys so much for listening today. I'm Ashley. He's Tony. and we'll see you guys on the next real estate rookie episode. At some point, your little real estate side hustle stops feeling little. Rent's coming in, maybe you've got a couple properties now and suddenly the money part gets real. Your tax bill's going up, you're Googling LLC versus S Corp at midnight and you're just hoping you didn't miss something that'll cost you later. That's where Collective comes in. Collective is the first all-in-one financial solution built exclusively for solopreneurs, saving you time and money.

29:51Tony:They help you structure your business for success, whether that's forming a single-member LLC or adding an S-Corp election. Collective's AI engine, backed by expert oversight, automatically categorizes every expense so you never miss a deduction. Beyond bookkeeping, they handle quarterly tax estimates and prepare both your business and personal tax returns, so you never miss a deadline. You'll also get integrated invoicing plus seamless payroll for S-Corp owners, which can unlock thousands in self-employment tax savings. And with Collective's community and support, you can finally take the solo out of solopreneur.

30:22Tony:Right now, Collective is giving you 50 % off your first two months when you go to collective.com slash rookie. That's 50 % off your first two months at collective.com slash rookie.

30:31Ashley:Hey, rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie podcast. Now, look, you don't need to be an expert. You don't need to have done thousands of deals. Even if you've done one deal, your story could help inspire the next listener.

30:49Tony:As a rookie investor, especially if you just got your first deal, it is all fresh in your minds and you are the best person to tell your story, give your experience on how you got it done to help someone else get their first deal.

31:02Ashley:So head over to biggerpockets.com slash guest if you want to be a part of our show. Again, that's biggerpockets.com slash guest. And we'd love to have you on.

From the publisher

Want to finally buy a rental property in 2026? You’ve listened to the podcast. You’ve read the books. But what’s the best way to actually start? Today, we’re pulling back the curtain and sharing a beginner-friendly strategy that gives you a bit of everything—cash flow, appreciation, loan paydown, AND tax benefits!

Welcome to another Rookie Reply! We’re back with more questions from the BiggerPockets Forums. First, we’ll hear from someone who knows plenty about real estate investing but needs a clearer roadmap for getting started and scaling their real estate portfolio. Ashley and Tony share a rookie-friendly investing strategy that will help them not only buy their first deal but also get a head start on building serious wealth!

Another rookie has saved a large amount of money and is considering buying their first property in cash. But should they? We weigh the pros and cons of paying cash versus getting a mortgage. Then, we discuss the opportunities and risks of investing in D-class neighborhoods, as well as a few things all rookies should know before evicting tenants.

Looking to invest? Need answers? Ask your question here!

In This Episode We Cover

The beginner-friendly strategy that gives you cash flow, appreciation, and more

Paying in cash for an investment property versus getting a mortgage

Finding affordable areas to invest when you’re priced out of your own market

The biggest opportunities and risks of investing in “rough” neighborhoods

What every rookie should know before evicting troublesome tenants

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/rookie-685

Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 
Learn more about your ad choices. Visit megaphone.fm/adchoices

More from Real Estate Rookie

All 197 episodes
This “Hybrid” Rental Strategy Is a No-Brainer for Rookies in 2026 (Rookie Reply)Real Estate Rookie · 26 min
Listen in VO