$30K Houses That Cash Flow $800–$1,100/Month | Land Contract Investing with Jenni Vega

Jenni Vega (00:00)

So one phrase that I heard recently at a conference with the group that I’m investing in was that the people that succeed at the highest level have the most certitude. They have the most certainty. They don’t overthink, they don’t doubt everything, they don’t question everything, they just hear about a concept and they run with it and they do it. So I guess I would challenge any listener listening to this, how much certainty do you have?

about real estate investing and about whatever your chosen model is, because a level of your certainty is potentially going to be the level of your success with it.

Scott Bursey (02:06)

Welcome back to the *Real Estate Pros Podcast* powered by Investor Fuel. I’m your host, Scott Bursey. Glad you’re with us. And today we’re delighted to be joined by Jenni Vega, a pro in the vacation rental space. Jenni specializes in short-term and midterm rental operations, advanced property management, and sourcing creative cash-flowing residential assets. Listeners, you can expect to learn how to optimize your own rental portfolio.

And find those hidden gems in a competitive market. Jenni, welcome to the show.

Jenni Vega (02:37)

Thanks for having me, Scott.

Scott Bursey (02:38)

It is awesome having you here and to help our listeners get up to speed. Please give us the ninety second highlight reel of how your career ignited and where you’re pouring your fuel now.

Jenni Vega (02:48)

Well, I started in short term rentals. At one point in time I had eight. I have sold off a couple of those. I have five now. They’re all over the country. But I’ve pivoted and I now own soon to be twenty-five, thirty thousand dollar houses all over the Midwest. And this is a totally different model, and I love it. We sell the or we buy them to then sell on land contracts, contract for deed. So I have

Soon to be twenty five of these contract for deed, thirty thousand dollar houses. And then I have the five short term rentals. So I’ll have thirty. in about a month from now. We’re closing down a few in a little bit here.

Scott Bursey (03:26)

That is incredible focus, Jenni. Really appreciate you sharing that path that you have found, that path that you’re on. And really, what caught my attention about you was the way you’ve been able to transform underperforming properties into high-yield short-term rentals that consistently outperform the market average. You know, taking that a step further, when you look at your property management systems.

What do you consider the biggest competitive advantage that you have over other vacation rental operators?

Jenni Vega (03:58)

Well, keep in mind that I operate in two worlds. I don’t just do vacation rentals, but if we want to start with that, my advantages are design, unique experiences. Most of our homes are incredibly unique. we really went all out with our design and short term rentals are becoming more and more competitive these days. So you really have to

go all out, unless you’re in a not so competitive city. And we have two that are in not very well known short term rental areas where we don’t really have to compete. And those are pretty ordinary stays. but the rest of them that I own and all of them that I manage, I should add that I do manage five. I own five and I manage five are all pretty

competitive and designed really well.

Scott Bursey (04:44)

Love that. And let’s dig into the current short term rental landscape, if you will. Where are you seeing the most friction in your daily operations?

Jenni Vega (05:41)

I would say a lot myself and a lot of other owners are spending time where they shouldn’t. One thing I just decided recently was I should not be doing things that a virtual assistant can do. Like I shouldn’t be doing anything that a VA can do. A few months ago I found myself in the middle of a busy workday where I should be I should have been in a sales appointment because my full time job is sales.

ordering towels on Amazon. And I thought this is just utterly ridiculous. Why am I doing this? And so since then I’ve onboarded a VA and she does all the little things like filing little insurance claims for guest damage and different things like that. ordering towels that need to be replaced.

When the cleaner has to contact me about something, now they’ll contact her or our other assistant. So I’m trying to really get into the owner space, not like in the weeds space. So my goal with the management side and my own portfolio is that this should just be two hours a week. And if we grow like five more properties under management, maybe, four maybe three or four hours a week. but I really like this.

in the management side, I like this model because it’s highly scalable. And just add another VA here and there and they can even message the guest, my job should mostly be to oversee and owner relationships.

Scott Bursey (07:02)

Thanks for being so open about those hurdles and interested in with the midterm rental market shifting, what’s one creative asset class or strategy you think is being overlooked right now?

Jenni Vega (07:15)

midterm rentals are on fire. I mean, they’re great. We have one. actually, the first investment property that I ever bought in Milwaukee, Wisconsin, bought this at the end of 2019. And it’s a very ordinary property, you know, and Milwaukee is definitely not a place that most short-term rental investors flock to. it’s not that competitive. but the property does really well all year long, and it’s a midterm rental in fall.

winter and spring and then in the summer it’s a short term rental. So in the summertime we’re able to get, you know, up to four hundred dollars a night. and then in the winter, we’re able to get a little under three thousand a month as in midterm. so it just does great. I mean we only paid $160,000 for that property. so it’s those markets that most short term rental on the short term rental side

that most inventor investors don’t think about, that we kind of started with. So we don’t have to worry a lot about people flocking there and saturation issues.

Scott Bursey (08:14)

Speaking of short term and perhaps even midterm rentals, what’s the first step someone should take if they want to get into that specific niche?

Jenni Vega (08:22)

Well, there’s a lot of good Facebook groups I would recommend joining. There’s national short-term rental conferences, there’s great podcasts for short term rentals, there’s communities of people for whatever real estate investing type that you want to do that you should absolutely get involved with.

Scott Bursey (08:38)

And wondering if you could share what is the biggest external pressure currently impacting the stability of vacation rental revenue in your primary markets?

Jenni Vega (08:48)

gosh. Well, Airbnb itself is an external pressure. I mean, they’re making it more and more difficult, if we can be candid here. they now they are charging 15 and a half percent as a guest fee, which jumps significantly. it’s a little bit harder and harder to do Airbnb, which is why I’m a big fan of midterm rentals.

especially in certain markets. So certain markets that have a lot of seasonality, like Milwaukee, Wisconsin is a great example. like in the wintertime when things slow down. I live in Phoenix and luckily my air my vacation rentals under management. I mean, summer just ended here. They were booked all summer long, but I do have them on Furnished Finder just in case we ever need to pivot to that. but

yeah, the midterm spaces are great, especially if you can be near a hospital. the one that we have in Milwaukee is five minutes to a major hospital. So that’s why we get a lot of that midterm rental traffic, traveling nurses, that type of thing.

Scott Bursey (09:49)

When acquiring new cash flowing residential assets, what’s your metric for the deal of the day, your primary strategy?

Jenni Vega (10:38)

Well, my primary strategy has completely changed. I I’m not gonna say that I’ll never buy a short term rental again, but I went from I mean, short term rental girl and that’s all I wanted to do, to now I’m buying you know, thirty thousand dollar houses, sometimes less. I’m actually closing next month on a house, fifty seven hundred dollars. Okay, and the house is livable. I mean it’s pretty hideous looking cosmetically.

And it needs about $5,000 of immediate repairs. But I found a model, I found a group of other investors, and I am over the moon with what I’m doing. And I really think it’s my calling. I still love Airbnb. I manage them and I I’m gonna buy more Airbnbs too. But I really found this niche that most people don’t know about. And it sounds too good to be true that even when I tell other investors, they don’t even

Oftentimes they don’t even want to listen because they can’t even wrap their brain around it. You know, how you how can you buy a $30,000 house? most of these we don’t rehab. if we do, very little rehab. The one I’m buying next month that I just mentioned, that’s a that’s a rare one off, but most of them we don’t rehab, or if we do, it’s like a five bucks for something little. but that is the ultimate cash flow machine.

in my mind, could we you can buy a thirty thousand dollar property that’s gonna cash flow anywhere from eight hundred to eleven hundred a month. and then with a land contract, for deed model, I’m not responsible for those repairs. Now with Airbnb, you’re responsible for all the repairs. And so it’s a very different model and and it’s awesome. So I’m really excited about it.

Scott Bursey (12:21)

Do you ever walk away from a deal just because it doesn’t fit those metrics?

Jenni Vega (12:26)

yeah, all the time. Absolutely. Yes. Yeah. Especially like condition of the property, area. When I started out doing contract for deed, I was really eager just to stack my portfolio. I wanted to get to five, then I wanted to get to ten, then we have all these benchmarks, but now a year and a half into that side of the real estate investing business, now I’m

a little bit more picky. I’m either going to buy very deep or the property has to be very turnkey. I mean, the one I just mentioned, the one that’s not even six grand, that’s far from turnkey, but come on, it’s not even six thousand dollars. So we can make an exception there. but when I got started a year and a half ago, I was spending a little bit too much and not as picky. and I definitely am pickier now.

Scott Bursey (13:14)

That’s a great standard to have and it really keeps the risk in check too, Jenni.

Jenni Vega (13:19)

Absolutely. Yeah, it’s risky. It’s risky and that’s why my financial partners prefer to just be the lender on the deal and they make double digit returns and they don’t have to worry about, tracking payments and filling the homes and all of that stuff. It’s risky but it’s also very rewarding.

Scott Bursey (13:38)

And if you could fill us in on what does your professional network look like right now?

Jenni Vega (13:42)

Well, I come from the real estate world, so I do have a little bit of an advantage. I’m not a licensed agent, but I have a couple of businesses. So I do Cutco closing gifts, which is selling Cutco knives to real estate agents. And I’ve been doing that for decades actually, here in Phoenix and or Cutco for decades. And then I also have a *Real Producers* magazine here in Arizona in a rural market up north.

And I also as a result of this land contract business, just about a year ago, I started host a wholesaling business on the side just a couple hours a week. And I quickly saw how that immediately feeds my land con land contract business. And so just a few months ago, I brought on a partner, her name is Megan, and she is now running that business for me.

And she has blonde hair, I have blonde hair, so we call our business the Blonde Deal Drop. so she’s constantly finding off market properties and then she’s basically selling them or just selling the piece of paper to other investors in our group that does the land contracts. So we’ve got that going on. I’ve got yeah, everything I do is in the real estate space. So when I started both with Airbnb and the land contract business.

It was my network here in the Phoenix area that helped propel both getting financial partners because I had already knew a lot of people in the real estate industry. And so when you know a lot of people in the real estate industry, naturally you know people that understand real estate investing, people that raise their hand and say, I’d like to be a private money lender. I’ve, I want to do some passive real estate investing with you.

That type of thing.

Scott Bursey (15:22)

That’s a diverse network, Jenni. Thank you for sharing. And let me ask you this. We call it the money question. If you had to start your rental business over from scratch today with zero portfolio, what is the most effective action you would take to generate immediate cash flow in your first, let’s say, 90 days?

Jenni Vega (15:40)

I would focus on the land contract business a hundred percent. And I would have started earlier. I first read a book about it in 2023. And I remember reading this book and just telling myself, I’m just gonna sit on this. I I’m not gonna focus on this right now. And I always kick myself for waiting because what happened was I waited a year and started about 12 months after I read the book. And a lot of other investors in my group, we all

talk to each other about how like it’s a five year clock because we get five year loans on these houses. And so we’re all waiting, unless the ones, some pay in cash, but the ones that have in finance, I mean, we’re waiting for these, we’re waiting for the five year clock to be done. And I think it was just fear. And this is something that every investor goes through. No one wants to start something new. It’s painful, it’s uncomfortable.

But man, I wish I would have started immediately after I read the book about it.

So but hey, we’re here now, so can’t complain.

Scott Bursey (16:42)

And thank you for dropping that truth bomb right there for our listeners. And you really have given us a lot of great words of wisdom here today, Jenni. But is there any final words, any additional golden nugget or two you’d like to leave with our listeners?

Jenni Vega (16:56)

So one phrase that I heard recently at a conference with the group that I’m investing in was that the people that succeed at the highest level have the most certitude. They have the most certainty. They don’t overthink, they don’t doubt everything, they don’t question everything, they just hear about a concept and they run with it and they do it. So I guess I would challenge any listener listening to this, how much certainty do you have?

about real estate investing and about whatever your chosen model is, because a level of your certainty is potentially going to be the level of your success with it.

Scott Bursey (17:31)

That is some pure gold right there. And for our listeners that want to keep this conversation moving, stay in your lane or collaborate with you on future deals, what is the best way for them to plug into your pipeline and reach you directly?

Jenni Vega (17:43)

Well, my probably emailing me is the best way. So I’ve got a real easy email. jenniscoolrentals@gmail.com So J E N N I S C O O L and the word rentals at Gmail.

Scott Bursey (17:54)

Awesome. Jenni, thank you so much for joining us today on the *Real Estate Pros Podcast*.

Jenni Vega (17:59)

Thanks for having me.

Scott Bursey (18:00)

It was a pleasure. And to our listeners, we appreciate you. If you receive value from today’s episode, please subscribe. We’ll be fueling your tanks with the lineup of elite guests, just like Jenni Vega, who are accelerating and setting the pace for the rest of the industry. Until next time, keep your standards high and your vision clear. We’ll see you in the next episode, everyone.