House Hunters Chicago!

Chasing the ideal investment in the Windy City.

Photo by Muzammil Soorma on Unsplash

Nestled along the bustling boulevard, this enchanting multi-family home boasts a striking blue brick façade that exudes character and charm.

The exterior, adorned with elegant white trim and a personal favorite — a welcoming stoop — screams “curb appeal.”

Two sun-drenched bay windows reflect the lush greenery planted across the property in the middle of the boulevard. A charming patch of grass just beneath the first-floor window offers the perfect canvas for a small bed of inviting flowers, adding a touch of vibrant color.

Inside, the spacious layout of this centrally located three-unit property features a harmonious blend of traditional style and modern comfort. This hidden gem is a true standout in the neighborhood and a perfect retreat for families and friends.

It’s also by far the best option we’ve seen since we began our search for the ideal place to call home.

Taking on the complex world of Chicago real estate has proven to be even more challenging than I anticipated.

Our realtor, Cassandra, has sent me more than 100 properties. She thought I was joking when I told her that I only needed to tour one.

That’s how underwhelming the inventory has been.

And that beautiful, blue two-story on the boulevard? Unfortunately, we can’t afford it. Like most homes in this current environment, it’s overpriced. The harsh reality is that its list price is at least $50,000 more expensive than our budget allows.

It’s no wonder why, in 2024, home sales fell to their lowest level since 1955 for the second straight year.

We’re learning first-hand why so many Americans feel hopeless when it comes to buying a home.

With inflated home prices, high mortgage rates, rising property taxes and low inventory, prospective homebuyers like us must navigate a “Wipeout”-style obstacle course to begin building equity.

Here in Chicago, the challenges don’t end there.

Abandoned homes and empty lots rest next to some properties in the inventory. Other listings are abandoned homes, total rehab projects that we’re not qualified to shoulder or able to finance.

There are high-crime areas we must avoid, commute times to consider and neighborhoods sitting in food deserts and desolate corners of the city that could be hard to rent.

The non-profit organization we’re using to secure our mortgage, the Neighborhood Assistance Corporation of America (NACA), aims to provide affordable housing for low- to moderate-income buyers. Their focus is on purchases in low- to moderate-income areas.

Still, the price of two-unit homes start at $250,000, based on what I’ve seen. For an additional unit, add another $100,000.

Again, those are baselines — the minimum for entry.

We’re looking at a $350,000 purchase that won’t be in the hottest neighborhood and will likely require renovations.

And after all of that, we’ve still got to find reliable tenants.

Whew!

It’s a lot just thinking about it all.

But we’re not letting a few hurdles stop us.

Our mortgage qualification with NACA expires in late June, so we have four months to get to the closing table. This deadline has ignited a fire in me; if we don’t close by then, we must start the tedious process over.

For now, we’re having fun with the search as a family.

Parker’s first snowball fight and snow angels with Daddy on Saturday, Feb. 15, 2025. | Photo by Triest.

Two weekends ago, after enjoying our first snowball fight on Saturday, the four of us piled into the car and braved bitter cold again Sunday. We just had to see that move-in ready blue house on the boulevard. We didn’t even go inside; we drove around the house and the block it sits on to get a feel for the area.

Although the house isn’t right for us, I discovered the location might be perfect. It would keep us planted in the heart of the city, with a similar commute time to Parker when she’s with her mother.

Last month, we drove around Chicago’s South Side to view five properties. One held an open house on the Saturday afternoon that we happened to stop by. Naturally, we took the tour.

That was the day I learned that my lady friend Triest, with all her property manager experience, will be much more of a stickler with this home purchase than me. We barely made it four steps into the living room when Triest caught a bad vibe. One awkward step served as the giveaway.

The floor was uneven. Water damage, she said. Triest didn’t need to see anything else. The home was a non-starter. Nothing else throughout the jumbo three-unit property impressed her. All she saw was a money pit.

On the property’s disclosure report, the seller acknowledged that the home also had material defects in the plumbing system and asbestos on the premises. We saw with our own eyes the detached, two-car garage needed major repairs as well.

A few weeks later, despite it all, the property is now contingent at its list price of $349,900.

This is the landscape we’re up against.

Despite the challenges of the Chicago real estate market, our determination only grows stronger. We know our next great investment is out there, and we’re eager to find it.

With patience and persistence, we’re embracing this journey, one step at a time — and apparently one home at a time.