How A Full-Time Pilot Closes $1.6M In Milwaukee Single-Family Rentals

Twenty closings in a week sounds like chaos until you see the structure behind it. I’m Cole, a legacy airline pilot and military instructor pilot building a Milwaukee real estate portfolio on nights, weekends, and whatever layovers give me. This update breaks down a seven-day sprint that includes Blackhawk flights, my first Boeing 777 run from New York to Paris and back, and nearly $2 million in single-family rental purchases.

I walk through two very different deals. First, five stabilized houses on the same street, already generating over $10,000 a month in gross rents, bought for about $600,000 with a seller credit and a hard reminder that lenders still want skin in the game. Then I unpack the long, messy 15-home portfolio I’ve negotiated for two years: small houses with deferred maintenance, vacancies, unpaid taxes, and liens, but a clear value-add path with a targeted rehab budget and realistic rent expectations.

We also get practical about financing and risk. I explain why hard money can be the right tool when speed matters, what a cash-out refinance can and cannot return at typical 75% LTV limits, and how I think about exit strategies like holding for cash flow, selling, or using a 1031 exchange. If you’re trying to build rental property income while keeping a full-time job, I share the “boring” factors that actually unlock growth: credit, consistent income, and hiring a solid property manager early.

Subscribe for the closing statements and the full numbers, share this with a friend trying to buy their first rental, and leave a review if the behind-the-scenes detail helps. What part of this process feels hardest for you right now?

Transcript

Welcome And Week Preview

SPEAKER_00 0:00

What is up everybody? My name is Cole. I'm a part-time real estate investor, full-time legacy airline pilot, and a part-time military instructor pilot, documenting my journey as a pilot by day and a real estate investor by night, growing a portfolio in Milwaukee, Wisconsin. Welcome to Tailwind Talks. All right, everybody, today is an update video on the last week's worth of events. Um I flew the Blackhawk like five different times, I think, in the last week. I flew the 777 from New York to Paris and back for the first time ever. Uh, so there's a lot going on. And on top of that, I'm closing on my most properties in a single week ever. Uh 20 single families that are closing on Friday, which is tomorrow. So uh it's approximately$1.6 million worth of real estate. And I'm gonna explain exactly how that's all working out. And of course, after the closing, I'll upload all my closing statements and give you guys a true idea of what it actually cost me to do all this. But I'll kind of give you the idea. I'll do a tour video of the properties that I'm buying later. The idea though is that uh I am buying 20 single families, five of them in one transaction, uh, and 15 of them, it's quick math, uh, 15 of them in another transaction. Now, both transactions are are interesting, but for different reasons. The the five that are on their own are being purchased, they're already stabilized, they're already generating rent over$10,000 a month in gross rents. And I paid$600,000 for them. I asked for a$50,000 seller credit, uh, which helps offset my down payment liabilities. Can you always do that? No, not necessarily. If you do it all the time, some lenders will push back on you and say, hey, you're taking these credits, uh, you know, to assist with your down payment, basically. And that means that you're you have less skin in the game, and they don't necessarily love that because the whole reason that you put a down payment on a property in general is because the lender wants you to have skin in the game. Barrowing a VA loan, like I used to get this house, uh, barring something like that, you have to put a down payment down. So uh when you're using seller credits to try to offset that, usually there's a limit to that, and they want to see you still bringing money to the table so that way you have some risk in case things go wrong. You have a vested interest in the investment going well. So these single families though are all on the same street together. I did a video of these uh during the winter. It took forever for this to close. Sometimes uh you have issues, and our issue this time was appraisals. A lot of people quote three to four weeks for an appraisal turnaround from when the lender orders it to when it's actually back and the lender gets able to review it. This one took, I don't know, maybe 70, 80 days to actually get it back and get everything finalized. So it really got delayed. The person that's selling them I work with very often, I probably buy 60% of my properties from uh these two people. So they know me really well, they understand the deal, but it's frustrating for everybody and it puts me kind of on my back foot because I'm like, I'm ready to go. Like we have the money set aside, we have everything figured out, but I can't do anything about an appraisal, and I can't close a loan that size, of course, without an appraisal. No, no bank is gonna go on without an appraisal. There are some situations where they'll do like a review of property, like they'll go look at it and they'll determine on their own what they think it's worth. But that's really for small deals, usually, and that's kind of a one-off thing that doesn't happen super commonly. So that's supposed to close tomorrow. Again, I'll have a whole video with the closing statements, what I brought to the table, what the seller actually made on the sale, and uh talk about all that stuff, the details on it, and show you the pro forma, what I think the property is going to do as far as performance goes. Today, though, I want to talk about the other deal and kind of how I manage doing all these things at once. Because if you're watching this, you're likely somebody that also is working a job and is curious how could somebody like me with a normal full-time job, you know, two of them, how could I do this without, you know, some substantial resources or having a ton of money to start with, which I had neither of. But I want to talk about the other deal first. So 15 single families, I these things are like 672 square foot boxes, two bed, one bath, uh, no frills, not nothing exciting about these except for the fact that I'm getting them for what I believe to be an absolute steal. I've been working on this deal for two years, and I'm gonna do a whole thing about this again once they close. The whole premise was uh the seller wanted like 110,000 a house, and these things have seen better days. They they have been beat down. Uh, they they need siding, they need soffit, they need fascia. They some of them had water damage because they weren't winterized properly. They all need interior work, and uh, I'll I'll reserve any thoughts and feelings about the person selling the properties, uh, but they just were neglected. They the property taxes aren't paid on them for the last few years. They've just, you know, half of them are vacant. Um, they just weren't cared for very well. And so I think uh this person bought them for you know somewhere between 80 and 85,000 a house. And I think they thought they were just gonna kind of sit on them and they would just be worth more money because everything goes up, right? But in real estate, things can go down and they can go down really quickly. And the the unfortunate thing is uh these properties really are pretty solid, and I've seen people getting$1,200,$1,300 a month for these places, so super solid, strong rents, super great property for a first-time home buyer. You can get into these for about a hundred thousand on the nicer end, maybe a hundred and thirty or so. But these are really nice properties if they're well kept. If they're not well kept, just like any other property out there, uh, they quickly degrade. And at this point, I'm getting them at their lowest. So this all started two years ago, and uh the idea was that I wanted to pay$70,000 a house. I was not willing to pay a dollar more because I knew what I was walking into the necessity of probably$200,000 of work just to get them where they need to be. And so you have to stick to your numbers, and I stuck to these numbers for two years. I got offered$80,000,$85,000,$75,000, and we went back and forth, back and forth, and I just stuck to my guns. But I did give in a little bit. I ended up, we settled on$70,500 per house. So I gave in$500 a house times 15 houses. I gave up a little bit of money, but in my opinion, that's about as good as it was gonna get. I thought that we had gotten pretty close. This person had been squeezed. I mean, they had been paying their property taxes, they had been paying water bills, they've got DNS orders, they've got a$20,000 construction lien against these houses. Like this person needs out, and they've got me. So the premise of this deal is that I'm gonna buy these, stabilize them, rent them out, andor have the option of selling them off. Like I said, they're worth about$130,000 a house. I've got quotes back for the all the exterior work and I've got an estimation for the interior work. It all totals out to be about$15,000 a house. And if you do the math on that, the idea is that uh they're gonna be worth somewhere in the range of$1.9 million. I'm gonna owe between the purchase price and the fixes, maybe$1.25. You know, let's say we go over budget a little bit,$1.3 million. So you can do the math. There's a delta there of about$600,000. Now there's a lot of repercussions. If I sell them, I'm gonna get nailed for capital gains. If I 1031 them, then I have to find replacement properties within six months and have to identify them much sooner than that. You know, there's there's a lot of complications. The easiest answer for me is just to rent them out and stabilize them, enjoy the cash flow, and do a cash out refinance on the back end because I'm gonna be using hard money to finance this deal. So I'm bringing you know my small, small amount of money down to pay for the funding fee and everything. Um, but other than that, I don't have any skin in the game. So I'm gonna be paying high interest for a minimum of probably two or three months, a maximum of six months before the term is due. Um, and then I'll refinance on the back end. So there's pros and cons to everything though. If I do a if I do a cash out refinance, I'm limited to 75% loan to value. So on 1.9 million, let's say I even get lucky, I get 2 million. I can only take out so much money. I can only take out 1.5 something minus my expenses and my initial purchase price. There's uh there's money there for sure. And you're not gonna hear me complain about it, let's be clear. Uh, but it's not like it's gonna be the whole 600,000. You have you're limited usually to 75% loan to value, and for good reason. If you start getting into the 80s, into the 90s, your cash flow really starts to take a hit and you can get yourself into dangerous territories. As far as this deal goes, I don't know what I'm gonna do with it yet. And there's a lot of that in real estate. If you're getting into this and you're trying to figure out what you're doing and you're not sure if you're making the right moves, guess what? There's just a lot of what ifs, there's a lot of variables, and you just have to do something. And that's really the point that I wanted to get to with this video. In a span of seven days, I've flown Blackhawks, I've flown a triple seven to Paris and back, and I'm closing, you know, almost$2 million worth of real estate. It's possible. I'm not a genius, I'm not special, I'm literally the most average person in almost every way. Um, but it can be done. A lot of it has to do with your own internal drive and your willingness to kind of put in the work. People talk about, you know, working hard and putting in the work. What does that actually mean? Well, really, what that means is first off, getting educated. And if you're watching this, you're trying to get educated. You're doing a great job of that, I would say, because you're watching me, of course. Um, but a lot of it has to do with uh trying to put yourself in a position to allow a bank to lend to you and also have the knowledge to buy a good deal. Uh, that's putting in the work. That means figuring out what is a cash flow on a property actually look like. I can make a spreadsheet all day long, but what does it really look like in practicality? That means going out in your local city. I'm in Milwaukee. If you're in Milwaukee, hit me up. I'll try to help you out. But go to your in your local city and go hit up the top 10 property managers and say, hey, I'm looking at getting into this rental property game. Could you potentially, you know, talk to me and give me some advice and maybe be my property manager? And it might take seeing three, four, five different property managers before you find one that you click with and feel like is a good fit. Um, that's part of putting in the work. You don't need to be an expert. You can just walk in there and be like, hey, I'm looking at getting into rental properties. I've got a full-time job to try to pay for this portfolio, especially at the beginning. Uh, I need a manager, a full-time manager that knows what they're doing. And you can sit and talk to people in a 10-minute conversation, you can get a pretty good vibe on somebody generally, whether or not they're trustworthy, whether or not they're actually good at what they're doing, whether they're gonna provide what they say they're gonna provide. That's part of putting in the work. Um, and then as far as going to work, that's another part of it. You have to be lendable. If you don't have good credit, you got to work on getting good credit. That means paying down your debt, that means paying your debt on time. Uh, I I have plenty of debt right now. I'm trying to skim down a little bit, but on the, you know, I have a car loan, uh, you know, I have credit card debt from time to time. Like I'm not debt-free, I'm not a Dave or Amsey by any means, but you have to control it and you have to live uh, maybe not within your means, but within your ability to pay every month. Uh, because if you start having late payments, when a bank pulls that up and sees you're asking for two or three or five hundred thousand dollars on a rental property, they're gonna say, dude, you can't even pay a two thousand dollar credit card bill. How are you gonna manage this? So you gotta manage, you gotta control the controllables, if I was to say anything. Uh, I there's a lot of guys my age and and younger that want to be day traders, they want to do this, they want to do that, but it's not consistent, stable income in the in the eyes of a bank. I'm not saying that you're not a great trader, I'm not saying that you don't know what you're doing, but uh what I am saying is that having consistent, predictable income is huge for the bank. I mean, all these things are you know, I'm rambling a little bit right now, but all these things come together to to put together your initial first couple purchases. And once you get your first couple down, then it starts to become self-explanatory because you know what the expenses are on a duplex or a single family and you can kind of educate yourself in a way. Uh, but the big thing is finding a good manager. If you're gonna keep a full-time job, just get a manager. It's not gonna make a difference. If you get a if you get a duplex and you're like, well, I don't want to pay 10% to the manager, guess what? 10% of your gross rents for the year, you're talking maybe a thousand dollars, maybe a little over a thousand dollars. It's not life-changing money, it's not gonna take you from zero to hero. Just get the manager, get somebody that's competent, see if you even like them. If you self-manager gonna get to 40, 50 units and be like, I can't work and do this at the same time, I'm gonna hire out a manager. And now you're taking everything, your whole everything that you've worked to achieve, you're taking handing over the keys to somebody and hoping that they do a good job. So test it out. Go go get a manager. If they suck and it's a duplex, you could probably survive, especially if you're working a normal job and make that mortgage payment until you get it stabilized elsewhere. So, manager, having good credit and keeping a stable job and having stable income, at least to show the bank one time. You for the first deal, I would highly recommend that. And honestly, even where I'm at right now, I think by the end of this week we'll be at about 12 million dollars in real estate. I still got my full-time job. Uh, it's easier to have this job than it is to work other jobs. Uh, speaking from experience, I used to deliver mail for the post office. I used to work at five guys, I used to be a dishwasher. Like, I did those jobs that suck, but they did lead me to where I'm at right now and where I plan to be in the future. So uh, as much as it might suck in the moment, um, I do think it's worth doing. If you're trying to build a real estate portfolio, what I've done and what I'm trying to do is extremely predictable and easy to replicate with some varying degrees of success. If you're in California or New York, it's gonna be tougher, of course. But as a general rule of thumb, these are simple principles that you can live by and really not have too many issues. And with all that being said, all these little pieces of advice that I'm just kind of rambling about, all this is uh blanket stuff that you could apply to anybody, uh, but everybody's situation is gonna be different. And so I actually got hit up for the first time for a consulting call from one of the people that's been watching my video, which was awesome. Uh something that I was kind of like planning on doing at some point, maybe, uh, but I wasn't really sure if there was gonna be an audience that really wanted that. And I'm certainly not, like I've said before, I'm not selling a course or anything like that. Uh, but I do think that some of the one-on-one conversations could be really valuable. Ben Mala has done it to the to the tens. Um, he really knows what he's doing. He's much bigger than I am. But sometimes what works for somebody that's at that level at the two, three hundred million dollar range, does not necessarily translate to somebody at my stage or below. With all that being said, uh, if you are interested in trying to talk about this stuff specific to your circumstances, uh, I'm totally open to doing some sort of consulting call. And uh if that you find that interesting or think that it could apply to your specific scenario, just let me know. Shoot me a uh message in the comments, and then I'll I'll give you my email and we can hit up from there. That's kind of the basic idea of what's going on right now with a small rant about how to actually do this. And uh tomorrow I'm gonna have all the numbers, all the figures, pictures, videos of all the properties, and we'll go from there. So as always, I really appreciate you guys watching, and I'll talk to you soon. That's the dog yelling in the background. See you guys. If I'm able to do that, then I'll be able to Kevin. If you can cut this out, the the dog is nudging my the puppy, the golden retriever is nudging my hand. Um so I'll try to reset that. I was trying to ignore it, but it became too much. Um if you really want to build a business. So um Kevin, I got I got another dog rubbing up on me. And uh you might be able to see him poking his head out there. What's up, buddy? Um get out, get out, get out, go just knocked over the light.