Quote from @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-UnitAround ~$720KLegal 3-unit (top, middle, garden unit)Market rents: ~$2,300 / $2,300 / $1,400–$1,600Total around ~$6,100Amazing neighborhood + great appreciationBUT the garden unit gets discounted by lenders → lower usable rentDTI hit ends up around ~$1,500/moOption 2 — Jefferson Park 3-Unit + Coach HouseAround ~$735KLegal 3-unit All units above gradeMarket rents: ~$6,200–$6,700 totalLender counts the income much betterDTI hit around ~$1,250/moMuch easier to qualify for my next propertyMy goal:To scale fast — buy again in 18–24 months, then keep stacking 2–4 units.My dilemma:West Town = stronger appreciationJefferson Park = better DTI + better underwritingRents are similar, but lenders treat garden units and coach houses VERY differentlyIf 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?

If you're in the middle class or lower it's cheaper to do nothing.We have a listing that's $189k, fully remodeled, with a park across the street.

The green area in the middle.  

It is 2019, middle of March, and I just got this brochure for the same project.

I finally found a property that will cashflow, im in the middle of getting multiple quotes for the rehab work that needs to be done.  

Our goal is to install a small 2-person island/counter in that area and hide all wiring so there's no visible pole in the middle of the room. 

I would avoid condos all together (saying that, I am in the middle of buying one.

@Moustafa Daghash I am in the middle of closing this one ,If it didn't sell i'll definitely reach out , Thanks anyways  !

utm_campaign=11.18.25_REINewsletter&utm_medium=email&utm_source=lterable&utm_channel=28425&utm_content=Marketing&user_id=The article lays it out clearly.On one side, you’ve got the cash-flow loyalists.On the other, the appreciation purists.And in the middle, a cautious recommendation to blend both and pray you find the right balance in 2026’s unpredictable landscape.The analysis is solid, but it left me thinking; What if you didn’t have to choose at all?

I’m definitely cautious about jumping into something that sounds too easy, but I’m still trying to figure out if there’s a middle ground between fully passive turnkey and full-blown BRRRR projects.From your experience, are there any safer ways to approach a semi-passive strategy without getting caught in those risky turnkey setups?