Tailwind Talks
Tailwind Talks is a podcast for high-performing professionals who want to build serious real estate portfolios without leaving their careers. Hosted by an airline and military pilot turned investor, it dives into actionable strategies for scaling your real estate portfolio while balancing the demands of a full-time job.
Tailwind Talks
Rental Rehab Walkthrough In Milwaukee
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A $105,000 Milwaukee house can look rough and still be a strong rental if you know what to inspect and what to ignore. We take you on a real walk-through of a 3 bed, 1.5 bath single family property that should rent around $1,700 to $1,800 a month, with a renovation plan that aims to stay under $10,000. The focus is practical real estate investing: make it clean, safe, durable, and rentable fast without turning a simple rehab into a months-long makeover.\n\nWe start outside where the expensive problems usually begin. I talk through why skylights and other roof penetrations belong on your risk list, what rotted trim under windows tells you, and how little missing exterior pieces can invite animals and water. Then we get serious about drainage: clogged gutters and poor grading can push water straight toward the foundation, leading to basement moisture and long term damage. If you want fewer surprises, you have to manage water first.\n\nInside, we go room by room with a landlord-friendly rehab mindset. Think refinishing or cleaning floors, fresh paint, replacing beat blinds, fixing outlets, and deciding when “good enough” saves you time. I explain why ripping out a kitchen backsplash or flooring can create scope creep, how to refresh bathrooms without a full gut, and why an upstairs half bath can be a hidden value add. Down in the basement, we talk flood history, why finished basements can be a trap in Milwaukee, how to think about braced walls, and which mechanicals might hit your budget.\n\nIf you’re planning your first flip, buying your first rental, or building a buy and hold portfolio, this walkthrough gives you a clear checklist for evaluating rehab costs and risk. Subscribe, share this with a friend who wants to invest, and leave a review with your biggest “deal breaker” on a house tour.
Exterior Risks Skylight And Siding
Gutters Grading And Water Control
Living Room Quick Wins
Kitchen Choices Speed Versus Upgrades
Bedrooms Paint Floors And Smoke Clues
Main Bath Cleanup And Targeted Repairs
Loft Bedroom Skylight And Half Bath
Basement Flood Story And Bracing
Mechanical Costs And First Deal Advice
Wrap Up Long Term Strategy
SPEAKER_00What's up everybody? My name is Cole. I'm a part-time real estate investor, full-time legacy airline pilot, and part-time military instructor pilot. Today we are checking out one of my new purchases that closes on February 20th. It's a single family, three-bed, one and a half bath house. And uh basically this one's a pretty simple project. Most of it's flooring, paint, some exterior work, including crit grating. Uh, but the roof itself looks pretty nice, the gutters need to be cleaned out, and these little like overhangs. I don't know if you would call it an awning or what you would call it, but these have seen better days. So we're gonna try to clean those up or remove them. Uh the side of the house needs a pressure washing and uh just like some general maintenance outfront, but nothing major. Uh but I want to give you guys kind of an inside look of what one of these houses actually looks like and what I'm planning to do to it, what it's costing me. Uh, this one in it, for example, is$105,000, should cost me less than$10,000 to renovate it, and I'm hoping to rent it for maybe$1,700,$1,800 a month. So not too bad of a deal. It's just gonna take some time to fix it up and clean it up. Uh, but uh I just want to give you guys an inside look at what it looks like and uh go from there. So follow me on inside. All right, real quick before we go in, I meant to mention the skylight up there. When I first saw this house, I saw in the pictures uh on MLS that it had a skylight, and normally that would be like totally against what I would want because if you have anything that breaks apart a roof, it usually means it's gonna leak. And if it doesn't leak now, it's gonna leak in the future. Uh and it costs money, obviously, to replace that and then put the shingles and everything over the top of it. So when I saw that, I wasn't super keen on it, and I figured this house must just be leaking a ton of water. Uh, but I actually, when I went inside of it, I didn't notice that. So uh just something to point out if you see things like that, a lot of times houses with chimneys, there's a lot of them in Milwaukee that have chimneys, uh, they always leak because the flashing uh gets damaged and then water seeps in and ruins everything. Uh, that's the same case with these skylights. So keep that in mind if you're ever looking at a house that happens to have those, it should be at least something in the back of your mind to say that I'm probably gonna have to replace this at some point, hopefully not now, but uh at some point it's probably gotta go, even though it is a nice feature. Um, so walking up the house, I noticed right away that there was some cracking in the block right here, uh, which kind of concerned me. We'll see later. That is no longer a concern for me at the moment. Uh, but that is something that you should note when you're walking up on a house. I'm looking at the siding, I'm looking at the windows to see how old they are, uh, and just general condition and security. If you see the upper window has like a bunch of rotted wood underneath it, so that's got to get addressed because things like rot do not get better with time. Uh, but more concerning to me was originally this uh this little bit of you know, there's a basically a hole here between where the blocks meet, uh, and it's kind of curved in. So that means that there's some movement in the foundation wall. Um, I don't claim to be a foundation expert, uh, but that does tell me that maybe there's something wrong that I'd want to consider. Um, but as I walked up, the driveway is in generally good condition. It's cracked up and whatnot, but it's not totally falling apart. There's central air in this house, which is probably gonna have to get replaced at some point, if not already. Uh, it certainly looks like it's pretty old, uh, but it's a small unit, so it's not gonna take a whole lot of effort to replace that. While we were talking about the AC unit here, we started laughing because we noticed that there's an inflatable ghost here, which really is a nice piece of decor and by itself makes this health house worth exactly what I'm gonna pay for it. So I'm definitely gonna hang on to that, maybe put it out in the front lawn for some of the you know advertisements for the the listing. Um, but as you can see back here, I mean there's a giant branch that's gotta get addressed. Uh the garage door has seen better days, but the garage itself didn't seem terrible. Um, a couple other little things. A lot of times these little pieces come off. Um, you can see this one's like ready to come off by itself. This one's okay, but this one's barely hanging on, and these ones are already missing. So you want to address those, you want to get those cleaned up because uh animals can get in there, water gets in there, and all that stuff takes a toll on the house. So there's just like a lot of little general maintenance things that have to get worked on. Um, because whoever lived here, you know, whatever, something happened for whatever reason they didn't want to live here anymore, and they kind of just left it abandoned in some ways, uh, and didn't really take a whole lot of care of it, probably while they were here. The gutters are full of leaves. Another thing, gutters full of leaves leads to water not getting uh directed where it needs to, and that leads to your basement uh potentially having water issues. So cleaning those gutters out is a key piece. And these are all things that I'm gonna pass along to the management company uh because uh the sooner you can address these, the sooner you can uh clean this place up and hopefully keep it for a long time. And if you just leave this stuff unattended, it's just gonna make the problems that this house already had worse. Um, and speaking of the basement problems, you can kind of see if you look at the the grating of the house, there's no pitch to it. So the water is all pitched towards the basement, uh, which just causes the basement to have more and more problems. So um we need to get grading in here. We need to lift the grade up and bring in a bunch of soil and you know, some sort of sod or something to hold the soil in place so it doesn't just wash away. And uh, we want that pitched away from the house towards the yard here, so that way the water drains properly away from the house. So these are just some of the things that come to mind when you look at a house like this. It's a small house, but you can see uh the the projects add up quickly. So you're ready to make them like they used to anymore. This is a nice little one, so perfect. All right, everybody, welcome to my humble abode. This is the living room for this house. You can see beautiful original hardwood floors that need to be refinished, uh, bunch of stuff just hanging off the ceiling. I mean, this is gonna come down. Uh, this is, I mean, we got some plumbing pieces here that are kind of just tactically left behind. That's kind of cool. Um, some pine shims, that's kind of cool. They left those behind. We can actually use these, so that's nice. And if you look nice and closely, you can see what we call the landlord special, which is a little bit of paint tactically all the way around the outlet, which we love to see. You're gonna rip down these you know curtains, if you want to call them that. You're gonna rip all this stuff down, you're gonna leave it empty, or potentially put your own in for the tenant to decide to do. Uh, but this portion itself is really there's not a whole lot to do. Fix out some of the outlets, paint the place, clean up the floors, make it look nice. Um, not a whole lot to do. As we move into the kitchen, we've got some lovely uh tile, fake tile flooring. It's not too bad. Uh there's a couple pieces that needs to get rectified, otherwise, you could just do the whole floor. Uh, but if you do the whole floor, it kind of turns into a larger project. You're gonna have to rip out all the trim, which is still original, and you know, it just makes for a longer process. Uh, and same thing with the backsplash. Is this the most beautiful backsplash of all time? Like, absolutely not. But um, if you rip all this down, as you can see, it wraps all the way around the kitchen. So if you rip it down, you're gonna have to redo all of that. Probably just drywall and texture uh up until the point that you get to here. But then once you get here, if you rip this out, you're gonna have to replace it with something. And it might seem like a simple job, but it starts getting kind of tedious and it's gonna add a lot of time before you can move somebody into here. So it's one of those things you gotta weigh the options of is it worth pulling it out? Is it worth leaving it? Uh, same thing with the cabinets. Are these cabinets like beautiful? No. Are they good for a rental unit? Probably because people, you know, sometimes beat stuff up. Um, but if you wanted to do the floor and maybe the backslash, then it might be worth just ripping it all out and starting fresh. But honestly, the way it sits right now, it's really not that bad. It should be a relatively, you know, it's basically cleaning, getting the appliances all set up properly, fixing up some of the cabinets, making sure there's no leaks and whatnot, and then you know, generally cleaning up, painting everything and moving on. All right, so now we're in one of the bedrooms. Again, as far as bedroom rehabs go, the blinds are beat up. I would probably replace the blinds for sure. That goes for these ones too, because they they've seen better days. Um, get rid of all this random stuff that's on the ground. But really, what it comes down to, these floors are actually not that bad. I would try to clean them. You could have somebody try to fill some of the gaps and try to make them look decent. Um, I wouldn't change the color or tone or anything of them. I wouldn't I wouldn't do anything. That I would try to clean it as best you could and fix things where they need to be fixed. Uh, and then I would definitely paint these walls though. You would be amazed at what you can accomplish with with some paint. The the staining and stuff I see up here and on the walls tells me that maybe people smoked in here. It doesn't smell very smoky, but it does kind of have that familiar symptom. So um, but you can see like there's a some drywall repairs, if you want to call it that, that never got mudded and never got textured. Um, and I don't even know how well this was done. But these are the kind of things you want to address. You want to make it as clean and as presentable as possible, uh, so we can give it to the tenant in a condition that they would actually want to live in. All right, so walking out of that first bedroom, we got ourselves a nice deep closet. Not a whole lot to do here. Obviously, paint it, clean up the floors. Same story as the bedroom, just uh in a closet. Then we move into another bedroom. This one I did notice there was uh drywall, drywall repair, uh, which means that something happened here that caused them to do that. That could mean that there's a rook roof leak, there could be an issue. Um, but at the moment, I don't really see uh you know any further damage, but who knows when they put this in? They could have put this in a week ago, they could have put this in a month ago. Um, so as we go upstairs, we'll kind of talk about the things that come to mind. Uh, but this bedroom really isn't a whole lot to do. I mean, it's a lot of the paint, you know, replacing some of the outlets, uh fixing these closet doors are like just I mean, you can't even move them. Uh so doing all that kind of stuff uh is basically required because you don't want to leave people with this tacked to the walls and try to give them to the give this to them as a rental. Um, and then that means replacing that window, probably too. I mean, there's just like a lot a lot of little things, but as you can see, it's not like we're doing a full renovation. This isn't a burnt up unit or anything. We're just we're just trying to clean it up uh that way it can be usable. But when it comes to the bathroom, uh you can see the tile is original and it's actually not in bad shape. I honestly wouldn't mess with the tile too much. I would definitely clean it though. You can see that this has seen better days. The tub is okay. Uh if you could reglaze it, that would be a potential option. And then the flooring is probably where I'd go next. The flooring in the bathroom has definitely gotten a little bit of water intrusion, which has led to the drywall getting some moisture sucked up into it too. So I'd try to replace the flooring and probably that lower half of the drywall and then paint it, uh, potentially clean out that vanity. Uh, I don't know if it's really salvageable. You might have to rip it out and just drywall over it. Um, sorry, when I say vanity, I mean the mirror and the the wood build out, I guess. Um so there's not a whole ton to do in this bathroom, but you definitely need to uh you definitely need to do a couple things to try to get it cleaned up and usable for somebody. Right now it's not in a condition that I would want to present it to anybody. All right, so up here, this is the third bedroom. Kind of a loft setup. We've got uh some beautiful writing on the walls, certainly a kid's room at some point, it looks like with all the scribbling and whatnot. No flooring in here. This is all ripped out. It was carpet at some point, but it must have been pretty nasty. You can see all the stains and everything out here. And I noticed outside on the tree that there was a chain that was wrapped up on the tree. So I assume there was a dog at some point. Dogs peed on the floor, the floor got stained. Maybe the kids, I don't know. I don't know how dirty these kids were. But what I do know is that everything is ripped out, so it's a clean slate. All we have to do is put flooring in and put a new, maybe a new subfloor in some sections. Put new flooring in, probably carpet, obviously, because it's already tacked in for carpet, um, and let it rip. You know, we got a ton of storage up here that's actually in good condition. The skylight that I mentioned is actually not leaking. If it was leaking, you would notice certainly down here where the water would want to trend, it would be moldy, it would be gross, it'd be wet. But there's no issues with the skylight right now. So I'm just gonna let it be. I think it's kind of a nice skylights are nice, it adds a lot of natural light, it makes something feel a lot. I mean, if this didn't have a skylight, it'd be a pretty dark and kind of nasty room. Um, but the fact that it has it is actually kind of a nice feature. It's just that they leak and they oftentimes aren't installed correctly, which leads to problems. I I feel like in this case you can leave it and you can revisit it in the future. Um, changing out the fixtures, I mean that that fan is disgusting. We're gonna want to replace that. Um, but you can see it's not a ton of work. We're not demolishing things, we're not rebuilding things. Uh, we're putting in flooring, we're we're doing painting. I mean, these are things that most people could do if they watch the YouTube video. Uh, so if you're looking at a house for something that trying to get into as a first flip, this really isn't too bad. My first flip ended up being replacing bathrooms, replacing kitchens, doing everything. And that was like a little overboard. This one you could get away with a lot less um because a lot of it's in decent shape. The other weird thing about this bathroom, or sorry, about this bedroom is that there's a half bath up here, which is really uncommon uh for these Milwaukee houses to see one of these in like what would be kind of a closet area. Um, so if you take a look at it, it's got a vanity, it's got a toilet, it's super dark. There it is, there's some light. Um, and I think that it's worth keeping as a half bath. I mean, it'd be super convenient if you lived up here and this was your bedroom, that you could have a half bath right up here and you don't even have to go downstairs for it. Uh, but at the same time, it obviously costs money and time to try to renovate this to the point where um it would be usable. Uh, but again, we're talking about paint, we're talking about flooring, we're talking about cleaning things up. I mean, all things that most people could do um if they watch a YouTube video and had a little bit of free time. So if this is your first flip house, it could be life-changing. Um, I just my plan is to do a hundred of these if I can, uh, slow and steady. It takes time, it takes effort, it takes money, obviously. But this is uh this is one that I came across that I really thought was pretty decent. Uh, we'll move to the basement next to show you uh about that foundation stuff that we talked about, and uh we'll go from there. Now we're in the basement. Uh the basement here, um obviously you can see there's insulation. It was set up at one point in time. I believe this to be a finished basement. Milwaukee had what they called like a million-year flood or a hundred-year flood. It was a we had a ton of water issues. I had some water issues myself. Some people had some major issues. I'll include some pictures of some of the ones I got from the management company. People had caved-in basements, driveways were washing into their uh into their basements. It was just chaos. So, um, what I think happened here was this was finished. This was a finished living area, whatever. Um, and then the flood happened, and water rushed in here, damaged a bunch of this stuff, uh, got it wet at least. It doesn't mean that water was rushing in the windows or anything. It probably means that the sump pump failed, water backed up into the basement, and now you've got all this stuff getting ripped out. So, my plan is everything's gonna go. We're gonna rip out everything, we're just gonna make it an unfinished basement. The living area and the two fourth stories above us um are plenty for somebody to live in, and this can be used as storage. A lot of times we recommend people not to finish their basements in Milwaukee because this stuff happens, and now you've ruined everything that was down here. Uh, so the plan is to just rip all this stuff out. Um, the insulation's gonna go, all the wood framing for the finished basement's gonna go. This stuff will probably go, and we're just gonna have it a clean slate. You can see a lot of the stuff is hidden behind the insulation, but it's as simple as this to just pull down the insulation and see, okay, look at this wall. We got a little bit of cracking here, um, but it's not any major movement, and we don't have any step cracking or anything. So I I pulled these down while I was here and I didn't see anything that totally concerned me. And the side of the house that I thought was the worst, which is facing this direction towards the base or towards the uh backyard, this part is already braced. And so if you're a new home buyer and you're like, oh my god, this basement's braced, this is terrifying. I would much rather have a basement that's braced than not, especially in Milwaukee, because the cost of putting these in is probably at least for just this wall, probably four to five thousand dollars. I would estimate. And the fact that these are in here, this basement's these walls are not moving anywhere. This wall in specific is here to stay. Uh, these these beams don't generally fail uh for a long, long time. And you can kind of see that they haven't really moved since then. There's not been any additional cracking. Somebody painted this when they painted the beams, and it nothing's really changed since then. So I'm absolutely thrilled to see these here. Um, and I'm looking forward to not having to brace this myself because that changes the whole dynamics of this deal. Um, one thing to note though, like when you're looking at paint like this, I can see there's the the paint's bubbling up and chipping off of the uh off the block, which tells me that moisture is still getting to these blocks, obviously. And I and the basements are always at least somewhat damp. There's always moisture around them. But I really want to get to the grating on the outside of this as soon as possible because without fixing that grating, these problems are only gonna get worse. And even with having the beams, uh, you could still have more basement problems if you let these blocks deteriorate from constant water intrusion. So that's that's like one of the first things on the exterior is to just re-grade everything, redo all the mulch and everything that's around the house, bring it up so that way we don't have to worry about these problems in the future. But as you look at it, water heater, probably gonna have to go. It doesn't look super great. It's a lot of rust, it's not leaking right now, but also no one's using it. So, right now I would estimate that that's probably gonna have to go. That's about a thousand dollars for me right now through the management company. And uh, the only other thing really leads to is the the furnace. And the furnace looks like it's in good condition, it's relatively new, and uh we plan to keep it there. I don't see major mechanicals to have to fix, I see a lot of like little tiny things to have to worry about. We're talking about paint, we're talking about flooring, I'm talking about a vanity or two, some bathroom flooring, uh, ripping out stuff. I mean, these are things that anybody could do. When I started my flip house, that was one of the first things I did was rip out the entire finished basement because it also had water issues. Um, and that's something that you could do as a starter investor. You find a house like this and have small projects like that that don't take a lot of technical experience, uh, you can knock it out pretty quick pretty quickly and with little money. You know, if you're sticking all your money in to buy the house, you're putting all your money down to buy it, and you don't have a lot of money for supplies and materials. A house like this is a project that might take you, you know, three months to get done, uh, but you can do it with a lot of uh with a relatively low amount of money. Buying paint uh and doing a lot of cleaning yourself, ripping stuff out costs you nothing but your time and your labor. Um, so if you can find a house like this that just needs little odds and ends, um, it could be it could be a home run for a first deal. I appreciate you all coming with me to do this tour and hopefully give you a little bit of insight and some some words of advice to work with if you're working on your first deal or maybe your hundredth deal. Uh again, you know, I'm in the hundred unit range right now, and I'm still doing deals like this all the time because I think these little deals add up to big deals down the road. So, anyways, appreciate you spending the time with me talking, listening, and uh, we'll do it again soon. See ya.