How A Working Pilot Builds A Milwaukee Rental Portfolio

I just wrapped up Boeing 777 training and got signed off to fly the jet for real and the timing couldn’t be a better stress test for my real estate systems. When you’re gone for weeks, you don’t get to “run over and check” on a property. Something breaks, a contractor needs access, or a small issue turns into a big one, and you either have infrastructure or you have chaos. So I’m sharing the behind-the-scenes update on how I keep a Milwaukee rental portfolio moving while I’m focused on flying and staying current with military requirements.

I also get specific with numbers from a recent single family house purchase: $105,000 to buy it, a little over $4,000 in hard money fees to close fast, and a $7,889 rent-ready bill from my property management company. We talk through what that money actually covered, why basics like lock changes and gutter cleaning protect you from future five-figure foundation problems, and how reinvesting rental income can accelerate the long-term “snowball” without depending on quick flips. If you care about cash flow real estate, buy-and-hold strategy, and managing rentals remotely, you’ll get a clear look at the tradeoffs.

Then I zoom out to portfolio strategy, including occupancy, staying cautious about overextending, and a 1031 exchange plan that rolls about $111,000 from sold duplexes into six replacement single family properties. With a small funding gap, improved interest rate, and better-than-expected insurance costs, we’re on track to hit a huge milestone: 100 units. Subscribe for more real estate investing breakdowns, share this with a friend building their first rentals, and leave a review with the question you want me to answer next.

Transcript

Who I Am And The Mission

SPEAKER_00 0:00

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. So I successfully navigated the 777 training. I'm officially qualified and blessed off to go fly the plane for real. Truth being told, I have not flown it actually yet. So don't hold your breath. Who knows what's going to happen when I actually have to do the job for real? But as far as the simulator is concerned, I'm done with it. I got to go home, and here I am, as you can see. Uh it took me a while. It was about six weeks or so from beginning to end. There was a little bit of a delay because we had a simulator issue, which delayed my training because there's only so many simulators to go around, and a lot of people need them for a lot of different reasons. You have to imagine you have people that are doing new qualifications like me. You have people coming back for their annual re-qualification. You have people in the case of the triple seven, a lot of pilots don't land it enough. So they have to actually come back and get landing qualified again. But that being said, I was able to get done with my training and I'm really thankful to be done with it. There was even a moment in time where I went from six hours of training in the simulator for the triple seven, flew home to Milwaukee, and by 6:30, 640, I was in my military aircraft flying uh to get my night vision goggle recurrency redone. By the end of the day, I was like totally burnt out, but it was awesome. I was able to keep current with the military flying and continue to basically get through this course. Excited to go to a bunch of new destinations, places I've never been, doing things that I've never done. I've never crossed the Atlantic. So that'll be new for me. And while that was happening, this is a great example of why my property management company is so key to building this portfolio. I was gone, like literally physically gone, not in the state, can't do anything. If a water heater was broken or a furnace exploded or whatever, I wouldn't be able to be there and physically do anything, intervene in any way. If you guys might recall, just recently I did a tour video of a single family house that I bought, paid$105,000 for it, used hard money so I could close on it quickly and get the deal secured, basically. While I was gone at training, the property management company, I handed them the keys to this house and said, Hey, you know, like rent, you know, basically make it rent ready. We had to install flooring, we had to paint. It was everything from removing like a bunch of debris from the gutters to painting it to doing flooring. All that stuff needs to be done to get it rent ready for somebody. And I've got the numbers on my phone right now. The total that I paid for was$105,000. And I paid about$4,000, just over$4,000 for my funding fee for the hard money lender. It was required to get this deal secured. I ended up paying a little bit more because I needed to close the deal as fast as possible. And I didn't have to put any money down. It was 100% funded. I paid for the funding fee, but other than that, I didn't pay for anything else. So I went in, having to pay that in advance, and then I just handed the keys over to the management company and their bill just came in. And the total on their bill is$7,889. That included changing the locks, that included doing the gutter cleaning out and everything, like I mentioned. If your gutters aren't clear, they're not doing any good for you. And water is just pouring over the side of them, it's going straight to the foundation, it's going to cause even more expensive repairs. If you if it cost me$500 for somebody to go and clean out the gutters, I would much rather have that than a$10,000,$20,030,$40,000 foundation repair. And that's basically why I am so keen on it when I get new properties and I can see trees and things growing out of the gutters. You got to get rid of them. In this case, I paid a premium for having them redo the house and set it up. But at the same time, like how how cheap could I have done it? Could I have done it for$4,000? Could I have done it for$5,000? Maybe. So sometimes it's like you're gonna have to pay a little bit extra to get the job done while I'm doing something completely different that pays the bills. Um, and the reason that it works for me is because I'm using rental income to pay for this stuff. I might not be taking a check this month from that LLC, but the LLC just paid for all these repairs on a new property that then will start generating income. And you can see how the snowball quickly grows. So, long story short, I've got$116,889 into the house. And as you might be able to see now, the property rents for uh significantly more than what I paid for it. And the key there is this single-family house. Generally, they're paying for the water bill, they're paying for the gas and the electric. The what I'm paying for is usually the property taxes, of course, and the mortgage on the property. So your expenses are significantly lower than they would be in a multifamily building with a boiler where you're paying for the gas, the heat for everybody, or even in individual properties, let's say uh a duplex or a four-family things like that, you're still paying for the water bill on those properties. And the water bill on those is no joke. On a duplex, I usually estimate about$450 a quarter. It adds up when you start doing that math. Single families make a lot of sense when you're just basically getting rid of all that excess expense, and it's kind of like a triple net lease almost. Anyways, got that property stabilized, got it out on the market, it's rentable to somebody in the city right now, and I'm really excited to have that one done. It was kind of a quick project, and there was even part of me that said, Well, it's all cleaned up now, it's got flooring, it's got this, it's got that. I could just resell it, but it's not my game. As you guys all know, I'm not really into the quick flips anymore. I did what I had to do to get started in real estate, which was a couple flips, but since then, I honestly haven't done really any at all. It's been a lot of buy and hold, set and forget, and wake up on the other side. So, what's been going on otherwise? We've been stabilizing a bunch of units. Uh, the ones that we just acquired recently was 20 plus units. We're at a pretty high occupancy rate right now. I think we only have one, maybe two vacancies, and one of them I bought on purpose, like we just talked about. So we're doing pretty good as far as that goes. But I'm just kind of laying low and waiting to see how things play out because it from one month to another, things can change drastically, and I don't want to bite off more than I can choose. So speaking of which, we've got a closing that closes tomorrow, and I'll make a separate video about it. I won't get into all the details right now. I'll give you some top-down overview though. We had a chunk of 1031 tax-deferred exchange money sitting at the title company, which basically means I had properties that I sold and the proceeds from those deals stayed at the title company. I never got to touch the money, never got to see the money in my bank account. It sits at the title company, and then I go buy something else with it. And that money is used as the down payment towards these. So the money is sitting there from two duplexes that were sold, totals out to about$111,000. And lo and behold, I found some replacement properties. So six single families. You guessed it, more single family properties. The 1031 money that we have sitting at the title company isn't quite enough to close the deal. So we have a gap of about$29,000. So we're gonna fill that gap and then we're gonna basically close on these new properties, and they should cash flow pretty well. When I did the spreadsheets for these properties, I expected about a 6.1% interest rate. We're down to 5.75. And I estimated the insurance for six single families at about 10,000 a year, and it's actually about$4,000 less a year. I messed up the spreadsheet a little bit, but long story short, we got it squared away. It looks really good, and we're excited to close on that one too. So that's literally happening tomorrow afternoon. I'll make a whole separate video about that, talking about the the breakdown of the uh closing statement. Those units, though, we're closing on six of them. That's gonna push us to a hundred units. So I'm gonna make another video about the path from zero to the hundred units that we're about to be at because that's always been the goal to me. If I could get to a hundred units, I felt like it was something that I could really dedicate a lot of time to and maybe make it my full-time venture. I've since found out that's not really true. But a hundred units is a huge landmark uh in my mind, and it was always something that I wanted to get to, and it's taken me years and years and years and years to get there. So really excited about that. And the point of that video is gonna be talking about from day one, day or day zero, I guess, when I had my first single family house that was a foreclosure in Wawatosa, and how I slowly built that up and every single deal along the way. So I'll kind of give you just a top-down view though, deal one, deal two, deal three, and we're just gonna go through each and every one. And I'll kind of talk about the moves that we made, what what kind of thought process we had doing it, and some of the lessons learned because we definitely made some mistakes, we definitely left some money on the table, and uh we've been punched in the mouth one or two times along the way. So um, that's really the update, honestly. It's kind of weird. We're getting into this place where the snowball is really building pretty quickly now. For a long time, when you have, you know, maybe 10, 20 units, it's still a lot more than most people have, and I was really thankful for that. But it just doesn't produce enough to make it like a full-time thing, in my opinion. And I've talked about this a lot. I'm really thankful that I stuck it out and kept my jobs. I was working at the post office for a period of time. Uh, I was working um a very minimally paying uh airline job, and it, you know, COVID came around, that place went out of business, and there's just a lot that happened. But I'm really thankful that I saw through and stuck it out because that's what's paying dividends right now. Keeping that job, keeping both of those jobs between the military and my normal professional career uh and doing this on the side was the way to go. And I know I'm rambling a little bit, but the idea is that uh, you know, this was not an overnight thing. I still feel like we haven't really done a whole lot, uh, which is weird saying because I always thought 100 units would be the place, like, oh, this is where we want to be. And I'm very thankful for us being there, but it's just apparent to me that it's gonna take more. If you really want to build something, 100 units is is a lot, but people much bigger than that have lost everything. So I never lose sight of that, and I'm just gonna continue to grow and see where this takes us. Nobody gets out alive in this whole experience, so I'm just gonna go until the wheels fall off and see where that leaves me. So um, really appreciate everybody watching these videos. I know my last one, it had actually the lowest views of most of my recent videos, but it had a really long engagement time. So, those of you that are sitting down and listening to me ramble about real estate, I really appreciate it. If it doesn't come through in the videos, I really do love talking about this stuff, and I find this way more interesting than my day job, which is kind of funny. Um, but uh it really does mean the world to me that everybody sits here and watches this. That's the update. If you have any time or any interest, throw what you've been up to in the comments. There's a lot of people I've interacted with more than once in the comments. I'd love to know what you guys are up to. Uh, there's somebody I talked to recently who just closed on one of their first rental properties. That's a huge deal. There's people that have equity and they're trying to move it. There's a lot going on, and I'd love to interact with you guys in the comments because that's kind of where I feel like I get the most connection with people and can kind of help in some small way. So I really look forward to talking to all of you in the comments, and I appreciate all of you spending the time watching this, and I'll talk to you soon. See ya.