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My House Hacking Journey — Every Property, Every Move, Every Mistake

Jackson Krile · Flanders Team at RE/MAX Real Estate Center · Updated July 2026

A lot of people online talk about house hacking. Fewer people have actually packed their own boxes every single year, lived in a basement while their buddies rented the upstairs bedrooms, and patched the nail holes tenants left behind. I have. This page is the whole journey — the numbers, the moves, and the stuff that went sideways — pulled straight from the videos I've been recording since 2021.

“This is not some gimmick. This is real life — this is actually what I'm doing. And if I can do it, so can you.”— Me, on YouTube, back in 2021. Still true today.

If you'd rather hear it than read it, here's the video where I told the story start to finish:

The Timeline

Late 2018 – May 2019

Where it started: a license before a diploma

I grew up watching HGTV and always loved the idea of real estate. While I was finishing my business management degree (entrepreneurship minor) at Iowa State, everybody around me was lining up jobs and internships. I was studying for my real estate exams instead. I got licensed at the end of 2018 — about six months before I graduated in May 2019 — and joined the Flanders Team at RE/MAX Real Estate Center in Ames.

At that point I didn't really know anything. I was a sponge — learning from the people in our office, from podcasts like BiggerPockets, from YouTube. That's where I first heard about this “loophole” called house hacking.

“While everybody was getting jobs and internships set up for after college, I was studying for my real estate exams.”— “My Journey & Experience (So Far)”
June 2020

House hack #1: Ames — living in the basement, renting to my buddies

A year out of college, I saved up and bought my first house hack in Ames: a 3-bedroom townhome, purchased with owner-occupied financing for $211,500. I lived in the lower level and rented the other two bedrooms to two of my buddies from school, Bo and Robert, for $1,200 a month total — $600 apiece, utilities on me. That rent covered pretty much all the expenses: mortgage, utilities, HOA.

“I lived for free pretty much this whole last year.”— “Deep Dive Into My 1st House Hack” (2021)
$211,500
Purchase price
$1,200/mo
Rent from 2 bedrooms
~$0
My housing cost

And honestly? Living with friends was an absolute blast. If I'd been renting, I would have been doing that anyways — except this way, the house was paying for itself.

“After doing that for a year I started to realize — holy crap, this house hacking thing actually might work.”— “My Journey & Experience (So Far)”
2021

House hack #2: Ankeny — and the first property becomes a real rental

In 2021 I started looking for the second property. COVID had the market accelerating, but low rates brought real opportunity. We found a townhome in Ankeny (built in 2017) that had been listed at $208,000 and negotiated it down to $201,5005% down on a 30-year fixed at 2.25%, while the seller had bought it in 2018 at 3.75% with 20% down. Better financing terms are the whole engine of house hacking, and this deal is where I saw it play out on paper. This move was with my girlfriend at the time, Kat — she said yes to me later, but honestly the bigger miracle is she said yes to moving every year. Thank the Lord she's on board with this method.

The listing looked “under-rented” at $1,300/month when market rents for a 3-bed/3-bath in Ankeny were running $1,500–$1,700. Most investors saw a red flag; one text to the listing agent told me the seller was just renting to a friend. Being the buyer, the REALTOR®, and the investor on the same deal changes everything.

Meanwhile, the Ames property became our first full-fledged rental. Before moving out I put in new floors and carpet, built out the back patio with a gas fire pit and grill, mounted TVs — real updates, not just a rent hike for nothing. Rent went from $1,200 to $1,700 a month with tenants covering utilities (saving me another $250–$300/month), and the new lease was signed about 48 hours after listing it. Run the math and that penciled to roughly $800 a month in cash flow.

$201,500
Ankeny purchase (listed $208K)
$1,700/mo
New rent on Ames
~$800/mo
Projected cash flow
2022

Property #3: the off-market deal across the street

We loved the Ankeny neighborhood — the location, the neighbors, all of it. So we did something simple that most buyers never think to do: we asked around the neighborhood to see if anybody was thinking about selling. One of our neighbors was. We put together a great off-market deal, closed in 2022, moved across the street, and turned house hack #2 into rental #2.

“We started to ask around the neighbors to see if anybody was thinking about selling — and what do you know, there was.”— “My Journey & Experience (So Far)”

Fair warning from that move, though: we figured since we were just going across the street, we could skip the boxes and carry everything over with three or four people. In my own words from the moving-tips video: “No. It sucked.” Now we pack and clean one room a day until closing. Learn from my mistakes.

2023

Property #4: new construction in Ankeny — the snowball keeps rolling

In June 2023 we stumbled on a new-construction townhome in a different Ankeny neighborhood that checked all our boxes, went under contract, and closed toward the end of August — timed about 35 days before tenants moved into our old place on October 1st. That 30–35 day buffer is one of the most useful house-hacking habits I've built: there's almost a 100% success rate that you'll scrape a wall or find some issue moving out, so give yourself the runway.

By this point the earlier properties were generating enough cash flow to cover a big chunk of our expenses — and enough to set aside toward the next purchase. That's the snowball.

“Moving every single year isn't the most fun thing either — but I'm here to tell you, it is so worth it… If I could go back, I would have started as soon as I got to college. We'd probably have eight or nine by now.”— “My Journey & Experience (So Far)”
February 2026

Selling our first house hack together — the honest version

In February 2026, Kat and I closed on the sale of the first house hack we bought together — the 3-bed, 3-bath townhome in Northwest Ankeny, right off the Trestle Trail. (We first shared the decision in a video the previous fall.) This was always part of the plan: house hacking gives you the choice between holding for cash flow or selling to put the equity to work. We put the proceeds toward finishing the basement at our current house and paying off some higher-interest debt — because sometimes the guaranteed “return” of killing debt beats chasing appreciation.

But I want to show you the part most people edit out. When the tenants moved out, we found cracked doors, scratches, nail holes — little surprises everywhere.

“It's not all sunshine and rainbows. You got damages from previous tenants… I don't know what the heck they were doing — wrestling, or doing WWE in here — but I will tell you over and over again: it is all worth it. The little headaches feel big in the moment, but take a 10,000-foot view and they're pretty minor compared to the kind of return you can get.”— “We Are Selling Our First House Hack!” (Nov 2025)
Today · July 2026

Where we are now

House hacking built our rental portfolio one move at a time — four investment properties at its peak, every one of them a place we actually lived in first. In August 2025 Kat and I bought our current home in Northeast Ankeny, and in early 2026 we sold that first Ankeny house hack — right-sizing the portfolio on purpose, exactly the kind of choice house hacking earns you. And the same years I spent doing this for myself, I spent doing it alongside my clients: on the Flanders Team, Lloyd and I have closed 345+ transactions and more than $101 million in volume since 2018 across Central Iowa — first homes, buy-and-hold investments, house hacks, relocations, land, multi-family, and commercial — earned RE/MAX 100% Club recognition, and kept 5-star ratings on Zillow and Homes.com. First-time buyers, house hackers, and investors are my lane because it's the exact road I've been driving since I got licensed in 2018.

“The only thing I love more than building our portfolio together is helping others build theirs.”— “My Journey & Experience (So Far)”

Awards & recognition

Our work with the Flanders Team at RE/MAX Real Estate Center, recognized by independent industry rankings.

Flanders Team at RE/MAX Real Estate Center named to America's Best Real Estate Professionals by RealTrends and Tom Ferry, 2022
America’s Best Real Estate Professionals
RealTrends + Tom Ferry · 2022
Flanders Team at RE/MAX Real Estate Center, RealTrends Verified top team in Ames, Iowa, 2026, with Lloyd Flanders and Jackson Krile
RealTrends Verified — Top Team, Ames
RE/MAX · 2026
Flanders Team at RE/MAX Real Estate Center named Top 3 Real Estate Agent in Ames for 2026 by BusinessRate
Top 3 Agent in Ames
BusinessRate · 2026
Flanders Team at RE/MAX Real Estate Center ranked number 74 among Top 100 Small Teams in Iowa for sides and number 80 for volume
Top 100 Small Teams in Iowa
#74 Sides · #80 Volume

I help Central Iowa buyers do the same thing I did

Everything on this page — the owner-occupied financing, the roommate math, the moving playbook, the tenant headaches — is exactly what I walk my clients through, step by step, here in Ankeny, Ames, Des Moines, and the surrounding Central Iowa communities. Not theory. Reps.

If you want the full framework, start with my complete house hacking guide, and read how house hacking combats rising housing costs on the blog. When you're curious whether it could work for you, the House Hack Score quiz takes about two minutes — or just reach out and we'll run your numbers together. And the usual honest disclaimer: I'm not a lender, CPA, or attorney — for financing, tax, or legal specifics, loop in the right professional (I'm happy to connect you with good ones).

Want to start your own timeline?

A free, no-pressure consultation — we'll look at your budget, your market, and whether house hacking actually pencils for you.

★ ★ ★ ★ ★
Read all 107 reviews on Zillow →
Jackson Krile
Flanders Team at RE/MAX Real Estate Center · Central Iowa REALTOR®