How to Buy Rentals (Faster) with Real Estate-Related Skills (Rookie Reply)

0:00Tony:We take all types of questions, but today is a hard one to listen to. A rookie investor has realized that his first house has come with major buyer's remorse. Today, we will unpack his option.

0:11Ashley:We're also going to cover how to communicate with your tenant while setting boundaries and how to determine your next steps when you're feeling a little stuck as a rookie real estate investor.

0:25Tony:This is the Real Estate Rookie Podcast. I'm Ashley Karr.

0:28Ashley: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 work in the Asheville, North Carolina area for a small company doing custom remodels, mostly kitchens and bathrooms. I can do any labor that doesn't require plumbing or electrical licenses. I love my job and I'm thinking about how I can best leverage these skills to make greater future investments. I currently own one rental house that I manage and do all of the maintenance. What type of strategies and paths forward? If you were in my shoes as a professional handyman and home remodeler, where would you focus your time and energy to get the best return?

1:05Ashley:This question again comes from Jackson and the BiggerPockets forums. First, let me say, Jackson, I mean, dude, congratulations. You have one of the most desired skills in all of real estate investing. When you hear about a lot of the horror stories of being a rookie real estate investor, it's oftentimes tied to people hiring a general contractor or a subcontractor or, you know, handyman who disappears in the middle of the night with their money. You don't necessarily have to worry about that because unless you disappear on yourself, like that, that's not really a concern here. So if I were Jackson, I would take my skillset of everything aside from electrical and plumbing and use that to be the kind of sweat equity in a partnership.

1:49Ashley:And I would probably first focus on flipping homes to build up my cash reserves. And then once I've got enough cash, I'll start siphoning that cash off to buy deals myself. But dude, you've got a skill set. Like, man, I'll partner with you. I can go raise the capital in the deal. You do all the work. And then we got a beautiful partnership, right? So I mean, I would go out there and find a partner who can either bring the capital and then someone who can source the deals. And then you can be the person that does all of the labor and the managing of that labor.

2:16Tony:I'm going to say the opposite. I would not partner with you for having the skill set. I would say that there would have to be more to it than that because I'm putting up the money. I'm maybe signing on the debt. You're just spending time and doing labor. And like, yes, you don't, you won't get a payout if it's not finished, but you don't have skin in the game besides just your time you put into doing the rehab. And like, yes, that can be a lot. But what if you decide to take your time and you need to do other jobs because you need to make money now? So I would think of another way to add additional value or to be able to put a little bit of skin in the game.

3:01Tony:So maybe you are just putting in, you know,$10 ,000 or you're putting in some money so that you also have some skin in the game, but you're also running the remodel and things like that, too. I think that's a great idea to do the flips. The other option I would give you is to buy a house to live in as your primary residence and fix it up and either do a live-in flip or turn that into a rental property too. You have a great skill set to add value to this house and then sell it after two years and not pay any taxes on it because it was your primary residence for the last two of the five years. Or you could go ahead and add that value and then turn it into a rental at the end of year one.

3:45Tony:So I think those are several different options you have. You definitely have an advantage having the skill side. You can save so much money on labor where you're going to be able to make a little bit higher offer than other investors per se, because they have to pay for that labor where you'd be able to use your own time. And maybe just your, you know, So the electricians, the plumbers that you maybe have in your Rolodex that you can actually use can be an advantage to.

4:16Ashley:Ash, you are such a shrewd business person. And I love that point of like, hey, I guess in theory, they could still disappear in the middle of the night. Right. But they would just be disappearing on me, not on themselves. So I do like the idea of maybe trying to trying to get a little bit of skin in the game. um but i i think if and then and i guess this is the good thing about partnerships right like you can structure a partnership in any way that that makes sense right where maybe it is hey i'm going to pay you like an hourly rate on the deal like i'm still wanting to pay you like i would pay a person but hey maybe you're going to give me a slight discount so we can share and some percentage of the profits right that way because you're absolutely right i mean because they still got to eat right we've got to make sure that we got time to uh or money to keep the lights on so I do like that approach.

4:59Ashley:But I mean, the ability to do all of the work, there's an incredible amount of value for that. And for me, someone who lives in California, I've never bought anything in Asheville, North Carolina, having someone who's boots on the ground, knows the contracts or knows the contractors, knows the area, has a skill set. There is still a lot of value for that or in that for me as someone who's doing this remotely.

5:19Tony:Before we jump into the next question, let's take a quick break. When we get back, we'll go over tenant communication without losing your sanity.

5:27Ashley:There are two kinds of real estate investors, those who have reviewed their insurance and those who think that they have. Most don't realize their coverage wasn't built for how they actually invest. Vacancy periods, rehabs, short-term rentals, or LLC-held properties. These gaps surface only when filing claims. That's why investors work with NREG. They specialize exclusively in real estate investors, understanding portfolios, risk at scale, and cash flow protection. One claim can erase years of returns. If you own a rental property, don't assume you're covered. Have NREG review your insurance with someone who gets investing at nreg.com slash bppod.

5:58Ashley:That's n-r-e-i-g dot com slash bppod. Most investors spend more time chasing deals than reviewing their insurance. But a quick coverage check can be fast, easy, and one of the smartest ways to protect and even improve your property's cash flow. As the months get colder, frozen pipes, icy walkways, and seasonal wear and tear can increase the likelihood of claims. And traditional insurance companies aren't always built to handle these claims quickly or smoothly. That's why more real estate investors are turning too steadily. They focus exclusively on landlords, whether it's a single-family rental, a BRRRR builder's risk policy, or midterm holiday guests.

6:37Ashley:You get fast quotes, flexible coverage, and protection for property damage, liability, and even loss of rental income. Now is the perfect time to review your rates and coverage. Get a quote in minutes at biggerpockets.com slash landlord insurance. Steady, landlord insurance designed for the modern investor.

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7:30Tony:So our second question comes from the BiggerPockets forums. I self-manage a few single family rentals and a duplex, and I have been tracking all of my important dates in Google Calendar. The problem is I usually end up forgetting to send important documentation until the last minute, like sending new tenants, a list of utilities to turn on, or a move out checklist, and often end up having to manually print out a lot of paperwork and bring it with me to appointments. For those of you self-managing a smaller number of units, have you figured out a good way to do this without spending a fortune on software?

8:06Tony:So we actually, not too long ago, did an episode with Jamie Banks, and she led us through using a project management software, monday.com, and being able to set that up to pretty much do exactly this. So you would get reminders. A lot of this would become automated for you. So that is a great option. Personally, I use TurboTenant for my rentals. And when you move someone in, you go through their lease builder and actually build out the lease in there, it kind of guides you along with everything you need specific to your state. And then you can add all kinds of attachments into there. So all of this could be given to them when they do their electronic signing of their lease, they'd be able to get all of this at once.

8:53Tony:If you are a BiggerPockets Pro member, you can get RentReady, which is another great one for smaller multifamily that you can use too. If you have a smaller portfolio, where you can go ahead and put a lot of this into the software and have it send you reminders. It can automatically send things out to your tenants. And one thing that I really like with all of this software, not necessarily monday.com, but the two property management softwares is the tenant communication piece where not only can you send them documents and things like that, but it also has messaging in there too. So all of your messages with them is all in one place too.

9:35Ashley:Yeah, Ash, I couldn't agree more. I think having some sort of solution that automates the sending, like it's one thing to have it on your calendar to remind you it's another to actually put together the email, attach the proper documents and then send that off to someone. So I'm a big fan of Monday. We use Monday a ton. And to Ash's point, Jamie Banks just gave a great breakdown on that. I think the other thing that maybe you can look into, I mean, if you're managing a few properties already, you might also consider looking into a virtual assistant. And I know that people think that it's going to cost a ton of money to do that, but A, you don't necessarily have to hire them full-time to begin with.

10:15Ashley:I think the ability to find a really, really strong candidate goes up if you are paying them for 40 hours a week. But even if you bring someone on on a part-time basis, five to 10 hours per week, that's still work that someone's willing to take. And especially if it's for maybe lower level tasks or easier to complete tasks, like sending out emails and attaching documents, that's something that's pretty easy for someone to do. So, I mean, you could probably find a VA to do that work for four bucks an hour, maybe even less. So I would maybe even look into that because then they can all start helping you in other parts of your business as well.

10:47Ashley:And man, I know my life changed pretty dramatically once we hired virtual assistants. So I'm a big proponent of that as well.

10:54Tony:Yeah, actually, one, website that I've had a lot of luck with is BPM Solutions. And they're virtual assistants that are specific to real estate and property management. So they have certifications and training that they give to the virtual assistants that you can hire through that website. And you can literally hire someone for two hours a week. You don't need to hire them full time or commit so many hours. You can do it as you need them, but really easy process. Upwork is another one where you can find virtual assistants. And then there's like another company scale virtually, but most of the time you have to hire that person for at least full-time work through them.

11:35Ashley:We've used onlinejobs.ph pretty heavily for most of our sourcing. I think Upwork works really well if it's more like a gig based thing, but if you're hiring someone for maybe more recurring work, I feel like we've had slightly better luck with onlinejobs.ph just in terms of like the quality of the candidate. And obviously that website is focused on the Philippines, onlinejobs.ph, and for the Philippines. But there are other websites that focus on like Latin America. I have some friends who focus on VAs from Latin America. So you can go anywhere, but I think the bigger thing is trying to find the right person for what it is you're looking at and having time and bandwidth to train them up to do the things the right way is probably the biggest piece.

12:15Ashley:But virtual assistants help a ton, the right software in place helps a ton as well. The downside is both of those, I think, require some level of cost. I think the other thing too, and this is not to get too nerdy or to kind of go too far down a rabbit hole, but if you're at all paying attention to what's going on in the world of artificial intelligence and the AI tools that are out there, vibe coding is this phenomenon where you can basically talk to these different AI tools and they can build things for you. You can build almost anything that your mind can even potentially conceive right now with all the different tools that are out there, but not like lovable.dev or lovable.com now is a big one.

13:01Ashley:Base44, Replit, Cursor, if you're a little bit more tech savvy, but all of these tools allow you to say, hey, I want to be able to upload all of these different documents that get sent out on these specific dates. And then it'll build a tool that does that for you. So a little bit more involved, but from a cost perspective, significantly cheaper than the ongoing cost of a virtual assistant or some of the software that's out there. So just an option if you'd like to nerd out in that way as well.

13:29Tony:And that was a glimpse into what Tony does in his spare time.

13:32Ashley:The very little spare time that I have. You're absolutely right. I'm inside of these different tools, testing it out. We got to do an episode, I think, on how we're using AI. Are you using it much, Ash, in your day-to-day workflow? I know we use it for helping with content, podcasts, and all those things.

13:51Tony:Yeah. I mean, not to the extent you are. So, yes, I'd love to do an episode to learn. I mean, the biggest thing for me with AI is in hospitable, is using the app. To reply with AI. And so I have to talk to a single person and they do all my communication. That is like, I did this reel recently where it's like me, like waking up to a phone call or a text, you know, short term rental manager that me sleeping gracefully, putting my phone on airplane mode. Do not just stop whipping it across the room because I have so many of that messages for me. They're a little AI person. So that is like the best thing that's happened in my life as far as AI.

14:33Ashley:And for those that don't know, Ash and I both use Hospitable as our property management software. But they've integrated, as many tools have, with artificial intelligence, where they have this built-in feature where it'll scan everything that you've ever sent to all of your previous guests. You can give it all this additional information about your property. So that way, as new messages come in from guests, it can use all of that context to come up with a response. And you can either set it where you can review those messages before they go out. or if you trust it enough, it can auto send as well.

15:03Ashley:So to Ash's point, she's on just airplane mode, letting the AI.

15:07Tony:Yeah, I auto send all day long. But there was this not too long after we implemented it, there was a guest that messaged and said they were bringing a trailer with them and if there was room to park the trailer or whatever. And I was like, oh my God, I got to respond to this because it's not going to know. And I look and the AI responded to it. And it's like, when you pull in, there's a field to the left. you'll see the gate on the right side and a field on the left and you'll be able to back it in right there that you're working on like are they like pulling satellite images now the property like how does it know that but it must have been from like another message or something it was like the perfect answer and they're also like they there it's also so much like nicer responding like so thoughtful and things.

15:52And so, yeah, I enjoy it.

15:55Tony:I enjoy reading how pleasant and friendly I am to my guests.

16:00Ashley:If only they knew. If only they knew. But yeah, we should actually do an episode on that because I think there's so many different use cases for artificial intelligence. I use it like in my underwriting workflow where like if I'm looking at a market or if I'm working with someone who's looking at the market, one of the things I'll do is I'll take all of the data sources that we use, like AirDNA Price Labs, they allow you to get the, not the address, but you can get the latitude and longitude coordinates for all of the listings on whatever market it is that you're looking at. And that data becomes super helpful because you can start to build a heat map based on revenue of where the best performing properties are located within the market.

16:41Ashley:And before, I would take those latitudes and longitudes and go to Google Maps, and I just had to paste each one individually, and it was a pain. Now with one prompt, I can export all that data and it builds this interactive map for me where I can view very easily and I can see the revenue. So anyway, there's a lot of different use cases for AI. So we'll have to do an episode about that here shortly.

17:00Tony:Yeah. Let me think of what I need built and then I'll send it to you as an example. I've held it out.

17:09Ashley:Yeah. There's a multi-million dollar idea right there is where you just go to lazy millionaire real estate investors and say, hey, what tool do you need that I can build for you? And line out the door. All right, guys, we're going to take a quick break before our last question. But while we're gone, be sure to subscribe to the Real Estate Rookie YouTube channel. You can find us at Real Estate Rookie. That way you can see mine and Ashley's beautiful smiling faces every Monday, Wednesday, and Friday. But we'll be back with more right after this. There are two kinds of real estate investors, those who have reviewed their insurance and those who think that they have.

17:39Ashley:Most don't realize their coverage wasn't built for how they actually invest. Vacancy periods, rehabs, short-term rentals, or LLC-held properties. These gaps surface only when filing claims. That's why investors work with NREG. They specialize exclusively in real estate investors, understanding portfolios, risk at scale, and cash flow protection. One claim can erase years of returns. If you own a rental property, don't assume you're covered. Have NREG review your insurance with someone who gets investing at nreg.com slash bppod. That's n-r-e-i-g dot com slash bppod. Most investors spend more time chasing deals than reviewing their insurance.

18:14Ashley:But a quick coverage check can be fast, easy, and one of the smartest ways to protect and even improve your property's cash flow. As the months get colder, frozen pipes, icy walkways, and seasonal wear and tear can increase the likelihood of claims. And traditional insurance companies aren't always built to handle these claims quickly or smoothly. That's why more real estate investors are turning to steadily. They focus exclusively on landlords, whether it's a single family rental, a BRRRR builder's risk policy, or midterm holiday guests. You get fast quotes, flexible coverage, and protection for property damage, liability, and even loss of rental income.