Reflecting on my second year house hacking in Chicago

[Fed Finjap]

Reflecting on My Second Year House Hacking in Chicago

About a year ago, I wrote a post reflecting on my first year house hacking a Ravenswood 3-flat in Chicago. That first year was chaotic, stressful, and very hands-on. It was full of things I didn’t know to expect and mistakes I had to learn from in real time.

I ended that post by outlining a few goals: stabilize the building, eliminate PMI, tighten my systems, and hopefully be in a position to think about the next deal. A year later, I can say I made progress on all of those fronts.

Going into Year 2, I didn’t feel naive anymore. I had better systems, clearer standards, and a much better sense of what actually mattered. And honestly, this year was easier. Not because nothing went wrong, but because I knew how to handle it when it did.

Year 2 felt less like “figuring things out” and more like operating. And by the end of the year, I felt far less like a homeowner managing problems and far more like someone overseeing a small portfolio.

Q1 (Winter / Early Spring): Momentum, Progress, and Ongoing Drag

Compared to my first year, this period felt calm and productive, even with the garden unit eviction still lingering in the background.

I wrapped up a full kitchen renovation and sunroom update in my unit at the Ravenswood property. Living through that renovation wasn’t fun, but it significantly upgraded the unit and helped me feel like I was finally catching up on deferred improvements instead of just reacting to problems.

Right after that, one of the biggest milestones from my Year 1 goals happened early: I refinanced again. The refi eliminated PMI completely, brought my rate down even further, and meaningfully reduced my monthly payment by another $400/month. On paper, it was a huge improvement to the deal and immediately made the property feel more sustainable long-term.

That said, the garden unit eviction was still working its way through the courts, which was frustrating, but emotionally it didn’t feel as destabilizing as it would have a year earlier. I knew the process, had an attorney in place, and understood the likely outcomes at this point.

Behind the scenes, I also started getting organized with lenders and searching for another deal. This market was tougher than my first purchase. With the Fannie Mae 5% down option now widely known, inventory for 2-4 unit buildings in my target neighborhoods was thin, and good deals were going under contract quickly.

We focused more on off-market opportunities this time around. I placed an offer on a second investment property that ultimately didn’t happen. Disappointing at the time, but an important step in getting reps and clarifying what I actually wanted in the next purchase.

Q2 (Spring): Growth, Progress… and More Delays

Spring was when Year 2 really started to diverge from Year 1 expectations.

I finally went under contract on an off-market property in the Southport Corridor sub-neighborhood of Lakeview. Suddenly the idea of “maybe buying another deal someday” turned into something very real. During the closing process, I leased out the unit I had been living in at the Ravenswood property, officially transitioning that property closer to its intended income potential.

Meanwhile, the garden unit situation took yet another turn. The tenant delayed eviction through an attorney they obtained via the Law Center for Better Housing and ultimately exercised their one-time right to cure by coming up with roughly $15k in back rent through a rental assistance program. At that point, Chicago’s tenant laws require the eviction to be dismissed, so there wasn’t an option to decline.

On one hand, I got all of the lost rent back. That mattered financially. On the other hand, it was a reminder of how tenant-friendly Cook County can be and how little control you sometimes have once you’re deep in the process.

It wasn’t a clean win. It was a compromise.

Q3 (Summer): Portfolio Growth and a Different Kind of Intensity

Summer was the most intense stretch of the year.

Even then, it felt intense more because of volume than uncertainty. I knew what needed to be done and how to do it.

I closed on the Lakeview property and officially grew my portfolio. This was something I wasn’t sure would actually happen this soon when I wrote my Year 1 reflection. Almost immediately after closing, I moved into the Lakeview property… straight into a unit with a broken AC condenser in July.

What stood out most about buying the Lakeview property was how uneventful it felt compared to my first purchase. I knew how to work with lenders, what to scrutinize, how to underwrite conservatively, and how to plan the move-in. Even moving into a unit with a broken AC in July felt more like an inconvenience than a crisis. Annoying, but solvable.

Around the same time, I finally gave the garden unit at the Ravenswood property a notice of non-renewal. The tenants moved out in August, closing a chapter that had been draining time, energy, and mental bandwidth for over a year.

Re-renting that unit ended up being one of the clearest lessons of the entire year. By pricing it properly and holding firm on screening, I had multiple qualified applications and ended up placing a much stronger tenant.

The difference in stress level was night and day.

Q4 (Fall / Winter): Maturity, Leasing Lessons, and Stability

The final quarter of the year was quieter — in a good way.

I turned the first unit at the Lakeview property, pushed rents up, and learned firsthand how different the leasing dynamics are between neighborhoods like Lakeview and Ravenswood.

Around the same time, I also replaced the front porch at the Lakeview property ahead of winter. It wasn’t glamorous, but it was a necessary capital project that improved safety, longevity, and peace of mind going into the colder months. That kind of work felt very different from my first year. It was less reactive, more planned, and easier to absorb because the systems and reserves were already in place.

Back at the Ravenswood property, I renewed the new garden unit tenant after an initial short-term lease proved they were solid, and I renewed another apartment with a rent increase that was accepted without issue.

Those renewals felt like validation. Not just of pricing, but of better screening, clearer expectations, and firmer boundaries.

Looking Back on the Goals I Set After Year 1

The goals were directionally right, and execution mattered more than anything else.

• Eliminate PMI for the first building: Done
  
• Stabilize the first building’s garden unit: Achieved, but not without turbulence
  
• Optimize for management for when I move out of the first building: Still improving, but miles ahead of where I started
  
• Explore opportunities to expand portfolio: Ended the year owning a second 4 unit building within my buy box

Why Year 2 Felt Easier

Looking back, the biggest difference between Year 1 and Year 2 wasn’t fewer problems — it was fewer surprises. I had:

• Better tenant screening standards
  
• Systems for rent collection and documentation
  
• Established vendor relationships
  
• Clearer financial visibility
  
• Confidence in when to act and when to wait

Once the garden unit situation was finally resolved, the portfolio ran smoothly. Day-to-day management became quieter, more predictable, and far less emotionally draining.

Looking Ahead

Going into the new year, I feel far less like someone “house hacking” and far more like someone operating a small portfolio. Things feel calmer, more predictable, and increasingly passive. Not because I stopped caring, but because I finally built the systems to support scale.

My focus areas for 2026 are about tightening, stabilizing, and positioning — not rushing into the next thing:

• Fully stabilize the Lakeview property, with an emphasis on pushing rents toward market as leases turn, appealing property taxes, and continuing to improve the capital structure through PMI reduction or elimination and a potential refinance if rates cooperate
• Continue improving systems and delegation, so day-to-day management moves further toward a lighter-touch, portfolio-level role rather than owner-operator firefighting
• Position myself for the next acquisition in 2027, by strengthening cash flow, reserves, and financing readiness to be in a position to house hack another 3–4 unit property in neighborhoods like Lakeview, Ravenswood/Lincoln Square, North Center, and Lincoln Park

At this stage, the goal isn’t growth at any cost. It’s building something durable. A portfolio that performs well, doesn’t demand constant attention, and supports the kind of flexibility I was aiming for when I started house hacking in the first place.

For anyone early in the process: the goal isn’t to grind forever. It’s to build something that eventually runs without you.

[Caleb Brown]

Nice job! What a fun journey but you are doing it and making progress