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
June Rental Portfolio Breakdown – The REAL Income & Expenses from 60 Units
Ever wondered what real estate investing actually looks like behind the gloss of social media success stories? Drawing back the curtain on my 60-unit rental portfolio, I'm sharing every dollar that came in and went out during the month of June—something I wish someone had done for me when I was starting out.
The numbers tell a story that might surprise you. While some properties performed brilliantly (one duplex netted $1,654 on $1,700 in rent), others barely broke even or required significant expense outlays. A single running toilet caused a staggering $1,000 water bill at one four-unit property. Multiple units required pest control for mice and bed bugs. Five separate eviction filings cost $349 each just to start the process.
What becomes clear through this transparent breakdown is that scale matters tremendously in real estate investing. A single property that returned just $14.66 after expenses demonstrates why the "just buy one rental" advice falls woefully short—nobody's quitting their job on fourteen dollars a month. Yet when viewed as a portfolio, the performing properties balance out the underperformers, creating a more stable investment vehicle.
As both a full-time airline pilot and military instructor pilot, I've structured my real estate investments to function without my daily involvement. This means paying management fees and contractor costs that DIY investors might avoid, but the tradeoff makes financial sense given my primary income sources. When you're working 23-hour shifts as I sometimes do, spending $101 to have someone replace an outlet is simply practical mathematics.
The reality of rental property ownership involves constant decisions about rent optimization, maintenance priorities, and tenant issues. Should you raise rents on reliable tenants who are slightly below market rate? How do you handle the tenant who repeatedly clogs drains by pouring grease down the sink? These practical challenges rarely feature in investment seminars or YouTube success stories.
Want more transparency like this? Let me know in the comments if these monthly breakdowns provide value, and I'll continue sharing the unvarnished truth about real estate investing—both the wins and the headaches. After all, making informed decisions requires seeing the complete picture, not just the highlight reel.
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. Today I'm going to be breaking down all the income and expenses for my 60-unit rental portfolio for the month of June. We sold off a couple duplexes, so we're not quite at the 66 or 65, whatever I have in my bio. I apologize, but we're going to have that number back up after everything that went out the door the good, the bad, the ugly, all of it. It will be disclosed this month and then I'm going to continue to do that for the rest of the year and see if people like it, if you love it, if you hate it, leave a comment, let me know. I'm gonna jump over to the screen share off my computer so I can show you all the pdfs and we're 30 and blah, blah, blah all this non-practical advice for people trying to get started. And I'm here to show you the practicality, the real look inside of a portfolio that I wish I would have had back when I started, so you guys can make better educated decisions and buy properties that actually make money and so you don't waste your time like I had so often at the beginning of this whole journey. So, anyways, we're going to jump over to the computer, give you guys a look inside. If you love it, if you hate it, let me know and I'll talk to you in a minute. What is up everybody? Welcome to my computer.
Speaker 1:Now I've got the entire month of June written up all in here. I tried to do my best to include as much as possible, but I did want to be respectful of the company that works with me and the tenants' names. I felt it was most happens to be one that they use and I tend to like it. So we'll start off with this first property. It's got some information that's not included right now the address of the property, the money that came in, the money that went out and what I actually got from this property. Now this full disclosure, this number is before I pay for the mortgage, before I escrow money for taxes and pay for insurance. It's not exactly just the 1027 that you see there. There's other things that get subtracted out. So we'll go line by line.
Speaker 1:We got some rent income coming in, we got some more coming in, more we we retreated for mice. You'll see there's a couple of properties that have mice problems or rat problems and you could say it's a bad property. But honestly, a lot of times it's the tenants and the way that they live in these properties. I don't want to put full blame on them, but there's definitely an aspect of that that. If you leave garbage and open just food laying around and you leave your doors open and windows open things like that animals get in and they tear your shit up. We treated for mice 55 bucks, replaced vanity and drain pipes 425. That's expensive, right. We got some more rental income and then we got the credit back for the repair. I'm not sure exactly if this repair was something that the tenant was driving and somehow I got the credit back.
Speaker 1:Water bills aren't something that comes to mind. A lot of times. When people are thinking of a property and what it costs to own it, they're thinking of the mortgage, the interest and the taxes. Usually those are the three things that come to mind right away. But a lot of this other stuff treating for rats, fixing a vanity maybe, and doing some water bills you know that stuff, that's real life. That property is owned by me, so it's just a one page for that one and then we roll into the next one.
Speaker 1:This one's actually owned by an LLC. There's 12 properties in this LLC. Cash in is $19,797. We've got some cash out here about five grand worth. We'll keep going, keep it moving this one. We got some more rent income and then we got we replaced an outlet $101 and resetting a breaker.
Speaker 1:There's a lot of you sitting there saying $101,. I could replace an outlet for five bucks and that could potentially be true. The problem is I have a full-time job. Yesterday I left my house at 3am and didn't come back until 2am this morning. It's easy to say I could do this myself, but I would have to quit my job or not be at my job to do that, and what I'm getting paid at the airline is significantly more than what it would cost for me to be there to replace this outlet.
Speaker 1:So that's the cost of doing business. You're not only paying management fees, but you're also paying for this ancillary stuff as well. The upper here also got treated for bed bugs not ideal. That's something that happens. That's another one that's like some of it. Is it part? Is it partially? The property itself? Potentially, but a lot of times it's the people and how they keep their stuff. Do they wash their clothes and their sheets and do they change things out? How long they had their bed for? Where did it come from? Did they bring bed bugs from their last place? So there's a lot of nuance to that, but I don't even worry about it. I'm saying you know what? That's the cost of doing business. We're going to keep it moving, got the lower rent income, a penny for the late fee, and then repairing a fence and cleaning up garbage in the yard 137 bucks and then management fees. That's the eight percent that they charge. And then what I actually get was eleven hundred dollars from this duplex.
Speaker 1:Here's another one. We got a bunch of rent income in and then boom, 524 water bill. I mean those are quarterly but they're expensive. They add up. There's a lot of things that could cause your water bill to be astronomically high. This one isn't necessarily that bad, but if your toilet is running and not shutting off, that's a big one. That causes things. There could be leaks. There's all different ways that the water bill could be really high. Plus, the tents are using the water. That's just the way it goes. We only brought in $6.09, so our management fees are a measly $44.
Speaker 1:On this one. We got a portion of the late fee. Then they get the rest charge out for that and then our owner distributions are whopping $14.66. So this illustrates right here to me if you own just this property, if somebody on the internet sells you, you just need one property and you can be financially independent or you can quit your job. This is what you could expect to get $14. That's not enough to quit most jobs Definitely my job.
Speaker 1:Next property we brought in 2300. We only lost 356, so we saw 1900 of this one. Pretty good performance here. Rent income a bunch of rents coming in. We paid for some long care 150 bucks worth of long care not ideal, but again you got to keep the properties clean. You don't have to people don't do that, but I'm in it for the long haul management fees. Late fee owner another property bunch of rent income. This is a single family house. I know that one Adjust management fees on that and then we got $1,195 out of that one. So really pretty solid. I think I bought this place. I think, if this is, I think I bought this place for about 75 grand, so really not too shabby there. Next property a bunch of rent income. Water bills $337.96 on the water bills, management fees, proration of the late fee and then $1,300. So this one did pretty good too. Here's another one, $1,800.
Speaker 1:We had to do a little bit of plumbing some sink this is something that you'll see a lot of hair or people in their kitchens dumping grease down that clogs things up. We had one lady in the upper unit on one of these duplexes that was doing that nonstop. We went there three, four times before we got her to stop and we started charging her back for all those trips because she just wouldn't stop doing it. Here you go cleared kitchen sink drain line. I can guarantee you that potentially was due to grease. People put all kinds of shit down their sinks and into their tubs and their freaking toilets. You just never know. So plumbing is a big one. You're going to see that as a recurring theme here.
Speaker 1:Now, this is what I was talking about before. We got some cash in, a bunch of cash in, but then we did this high water audit. So they looked at my water bills and they're like, hey, this water bill is astronomically high. What astronomically high? What is the deal going on here? So they went and checked the faucets, the shutoffs, make sure there's no leaks. Check the toilets and that's the big one. Running continuously running toilets can just destroy your water. Your water bill leaks around the meter and the water heaters. There's a lot of places that you can look for this kind of stuff. And they checked it to see, okay, what's going on here, cause this property has got a pretty high water bill. And that's awesome that they do that, because it it costs me money, yes, but in the long term, this price between the water bill and the repair would be less, probably, than just letting things be how they are and continuously paying for water that's just being wasted.
Speaker 1:Dns repair. So this is the department of neighborhood services. They go around properties and they'll hit you with a fine and say, okay, you need to fix this or that. You could say, okay, you just have terrible properties, dude, but the d? They just pick and choose their battles and sometimes you're the flavor of the month and they're going to come and get you so $950 to do everything they did. You'll see here that both of these get cut off. You don't get to see the entire thing on this roll-up, but I could always ask for a breakdown if I needed to.
Speaker 1:But tough month on this one. Owner distribution on this is 285. So, again, if you bought this property, it makes $1,700 or so cash in. If you're expecting to see all of that, maybe you paid I don't know what I paid for this property, I'd have to look and see what it is. But if you bought this for 200, 300 grand and you're only getting 285 on this one, even though you brought in a bunch of rents, you had a. You know you need more than just one property to really make this work, because you have to be able to offset the bad properties with good properties. And this would be an example of a good one brought in 1700. We only had 143 of expenses, which was just the management fees, and we took home 1654. So you can see we're offsetting them with the bad with the good.
Speaker 1:Here's another decent one, pretty good, securing some loose carpet to the stairs for 55 bucks Again. Could I do that for my, for free? Sure, but it just doesn't pay for what I make in my normal job and the way that I've set my life up. I don't want to do that and I don't really think that it makes a lot of sense because this is, let's say, an hour job for me. An hour for me at the airlines is not $55. I can tell you that. Management fees and then 1508.
Speaker 1:This property, a bunch of income, management fees, distribution, pretty simple. Some of these are really clean. Here's a rent roll. So this whole, this is all one LLC. So now at the end you're going to see how the units break down. This is the rent roll. So this is a duplex brings in 1700. On this duplex, this one brings in 1790. This one brings in 2405. And for the most part our rents are pretty close to market. There's a couple that are a little low. These are three units. So this one and this one are three units.
Speaker 1:I've had these for a long time. When I say a long time, probably four years, but to me it feels like a long time. Solid, solid buildings, though honestly they're not super pretty, but they get the job done. Another duplex this one's a little bit below market rents. I know exactly what, what property this is. They've been the same since I've owned it. Probably bought it somewhere in this neighborhood, maybe a little bit after this, but anyways, they could be raised, but these tenants are pretty solid generally. I know exactly who this guy is. I've talked to him on the phone a couple of times back when we were managing stuff, and sometimes you have to weigh the benefit and cost of bringing these to market. If I bring these up to market which is probably $899 or so maybe $850, something like that If I bring these to market, the potential is that at least one of them is going to leave, and then you're gonna have to fix up their unit and rent it out, and so sometimes you look at that and say you know what, just leave it alone, we'll get that up to market eventually.
Speaker 1:Here's a single family for $1,300 a month $1,300 a month. Here's a duplex $1,798. Another duplex $1,870. Another duplex $2,190. Another duplex $1,700. Just under $1,800 for a lot of these duplexes. Another one for $2,000. And what is this? $2,048. Yep, all right. So now this is the next LLC. So this is two, three units in one LLC. We're on in $6,000. We had $800 in expenses, so we saw $5,200 of it. Got all our rent, income, paying for lawn care management fees, proration of a late fee and then distribution. Very simple, very clean. These are pretty decent buildings. One of these is better than the other, the other one's kind of crap. But income, lawn care management fees. Distribution, again very simple. And then here's the rent roll on this, this building in 4185. These are all pretty much market rents. Finally, on this building and this one's got some below market rents.
Speaker 1:I'd like to get these up so that they're matched. I bought these for 300 grand a piece, I think a little bit more than I normally would pay for something, but it was a good faith deal to try to secure all their stuff in the future. And they're all three bed, one and a half bath townhouse style. So these should all be probably, I'd say, at least $13.95, maybe even $14.50 you could get for them. So maybe I should look into moving these up, because there's a little bit of a delta there, maybe six, seven hundred dollars a month, which would be helpful. So I might push the envelope on these ones and see if I can get them moved up to market. But you can see they moved in january. This is all showing January 21st, 2024. I have to double check and see if that didn't all move in the same day. Sometimes this is just the way that it was input into the system. So I'll look into this one, but I'll keep you guys posted on this one. This one could have a little bit better rents. But again you have to weigh the benefits, because if somebody moves out it's going to cost a lot of money to reset a three bed, one and a half bath. Those are pretty big units and it might not be worth it. Here's the new LLC. This is a smaller one. It's a newer one.
Speaker 1:This one's a duplex that I just bought. One of the tenants had paid their rent by closing. The other one hadn't, so this is the one that hadn't paid the rent. So you see, it doesn't bring in a whole lot, but it's also an awkward month. And then it also transferred money from this property to this property, which had a bunch of problems. First off, the tenant did not pay their rent. They paid a little bit, but not very much, and then there was a blockage, so they had to clear out the blockage. You see, this cash in transfer from this money came from the above duplex to help cover this one for the month. So the ending balance was zero. So I didn't get any money, but I also didn't lose any money. I did because it any money, but I also didn't lose any money. I did because it got transferred, but you get the idea that's a nothing page.
Speaker 1:Here's the rent rolls. So this duplex brings in 1975. The single family brings in 1499. And this single family another new one doesn't show up on the report because nothing happened with it this month, but this one also brings in 1050. And this place cost me 68 grand. So we'll see how that one plays out, but it seems like a decent price. Here's another LLC brought in $1,9505, $5,700 in expenses.
Speaker 1:Let's go break them down. Bunch of income we got a repair for a missing trim on the roof management fees, proration of the late fees and then owner distribution on that one. Next one pretty straightforward on this one Income management fees distribution, income repair for a replaced water heater we must've got some prorated money off of it because of the exchange. Bunch of lawn care management fees, distribution. A bunch of income here, okay. So here's another one.
Speaker 1:People don't pay rent. Last month I had five of these $349 to file an eviction. And this is just filing the eviction. That doesn't mean that it's gone through. That doesn't mean that the sheriff's been ordered. There's more fees for all that stuff and this also means that you could have filed this eviction and then this person's going to pay up. It doesn't mean that they're getting evicted, it's just starting the process, and it's 350 bucks just to do that. So I had five of these last month.
Speaker 1:These are the things that you just don't really know are going to come up. You can't really plan for this. You don't know who's going to pay. You don't know who's going to stop paying. But in this case I took out a decent amount of money and this is why I always stress if you're a nickel and dime kind of person, you're counting pennies and quarters. There's a lot of people that swear by that and say that's how you're going to get business. I'm worried about the big numbers, I'm worried about equity. I'm worried about buying, I'm worried about selling and refinancing. If I got in a tizzy about every little thing like this that happens every month, I would literally go insane, like it. Just, it does not pay to worry about that, because whether you want it to or not, it's going to happen. And if you start bitching and complaining to your management company, they're just going to fire you and then you're gonna have to go find somebody else. So I think you just keep your mouth shut and just understand. That's the name of the business.
Speaker 1:We got some rent income, management fees, owner distribution, cash in on this one pest control. This one's got rats. This is actually a really nice duplex. I know this place. I was surprised to see this for this one, but again, it's hard to know why. There's a why behind this, and I'm paying for it, obviously, but am I the reason? Why? Is it the property itself that's the problem? Maybe not. They're saying they're coming from the basement. Maybe there's one of the glass block windows and the basement is busted out. Maybe it doesn't have glass block windows at all. But a lot of times that stuff has to do with the way that people are living in these properties. But this one's a really nice duplex. It was really well done. In any case, that's a decent price for those two.
Speaker 1:Both of these had two different pest control, two different pest control charges in one month management fees, a late fee, probation and then my own distribution was a thousand bucks on the eighteen hundred dollars of gross income. And that's before, like I said before, that's before you pay taxes, principal and and interest and then your insurance. Here we go. We got some windows, clearing debris, caulking gaps, and there could be more to this. Like I said they cut off sometimes. But income, that's the one. Expense, management fees, proration, late fees $1,300 on this duplex. Here's a four unit that I've got brought in, $3,800 and it had $2,000 worth of expenses and you'll see exactly what happened here.
Speaker 1:Bunch of income electricity bill this is just for the common area generally. With the four family You're just paying for the common area electricity, so that's why this bill is so low. Replace a toilet flange, wax ring that's not uncommon, I've seen a lot of those, but $250 to do that. And then the water bill with a $1,000 water bill. When you see a $1,000 water bill you have to wonder to yourself okay, what happened? What is going on here and you can see down here. They actually did an audit, but we got lawn care, cleaning the common areas, more lawn care, and then the high water audit. Looks like they ended up replacing the broken toilet handle and flapper. So one of these toilets was just continuously running and this is a great example of what happens when you have a toilet that runs nonstop. That is an expensive mistake, because $1,100 just for water that nobody used. If you get wrapped up around the axle about some of this stuff, it's going to make you sick. Late fee owner distribution on that one. Another one, nothing crazy. Here. Another water bill management fees, owner distribution income, lawn care management fees, distribution.
Speaker 1:A lot of these aren't too exciting. Here's a duplex, another duplex. These are all the rent rolls. This is a three unit. Another duplex, another duplex. This one's a little bit low on the rent.
Speaker 1:Another duplex, duplex, and you can see this is the three or this is the four unit. Rather, I love this place. It's a big four unit. It's a pretty solid building. It's a brick construction building. It's pretty nice.
Speaker 1:Another duplex, three unit, single family and that is that. So this is just June, so that's one month in the life. Like I said, sometimes stuff goes good, sometimes stuff goes bad. You, like I said, sometimes stuff goes good, sometimes stuff goes bad. You have to be prepared for the unexpected, because that's the only thing that's guaranteed in this game is that there's going to be unexpected things that happen and you're going to have to deal with them.
Speaker 1:When I see online people talking about what it actually costs to run a property, a lot of people don't really talk about a lot of these things that can happen.
Speaker 1:Thinking about a high water audit, like understanding your water bill and looking into why is your water bill so high? Looking into that something that a lot of people don't even think about as a thing that they would even want to care about. But until you get into this and you start seeing bills that are, like I said, a thousand dollars for that four family, then it's wow, water bills are important, huh? And so, anyways, it's just a look into this month. If you guys like these videos, I'll continue to make these videos. If you guys hate them, let me know the comments. If people don't want to see this, I won't show them, but I thought it was interesting just to give you guys an insight on what it actually looks like to run some properties. Again, this is 60 units, not the biggest portfolio of all time, but I'm doing it while working a full time job and then flying for the military part time. You guys could literally be doing anything on the internet, but you're here listening to me talk, so I always want to take your