Help Me Choose Between Two Chicago House Hacks

[Anne Connor]

Hello,

I’m deciding between two very different house hacks in Chicago and could use some experienced advice.

Option 1 — West Town / Ukrainian Village 3-Unit

• Around ~$720K

• Legal 3-unit (top, middle, garden unit)

• Market rents: ~$2,300 / $2,300 / $1,400–$1,600

• Total around ~$6,100

• Amazing neighborhood + great appreciation

• BUT the garden unit gets discounted by lenders → lower usable rent

• DTI hit ends up around ~$1,500/mo

Option 2 — Jefferson Park 3-Unit + Coach House

• Around ~$735K

• Legal 3-unit 

• All units above grade

• Market rents: ~$6,200–$6,700 total

• Lender counts the income much better

• DTI hit around ~$1,250/mo

• Much easier to qualify for my next property

My goal:

To scale fast — buy again in 18–24 months, then keep stacking 2–4 units.

My dilemma:

• West Town = stronger appreciation

• Jefferson Park = better DTI + better underwriting

• Rents are similar, but lenders treat garden units and coach houses VERY differently

If the Jefferson Park one looks good in person, I’m leaning that way…
But if it’s only average, should I just take the West Town one or keep looking?

Which would YOU choose and why?
Appreciate any input!

[Denise Supplee]

I'd look at it through the lens of your main goal: scaling quickly. Appreciation is great long-term, but if the West Town deal slows down your DTI and delays your next purchase, that works against the plan. Jefferson Park giving you stronger lender treatment, all above-grade units, and a cleaner path to buy again in 18–24 months is a meaningful advantage.

That said, don’t force it. If Jefferson Park looks mediocre in person, I’d keep looking rather than settling for West Town just because it’s the “sexier” neighborhood. A solid, lending-friendly property in an average area often beats a premium location that bottlenecks your ability to scale.