We're attracted to the city's openness to adding ADUs, etc to traditionally single-family residential zones.

Nashville STRs are such a hot space, and it sounds like you bring serious value with zoning, pro formas, and tax strategy support.

Zoning & ADU ConsiderationsChicago’s ADU Ordinance applies if you create an additional dwelling unit beyond the existing count.If you stay at 2 units total (just shifting one unit partially to the basement), you likely don’t trigger ADU rules—but confirm with zoning since each ward can interpret things differently.If you want to eventually rent the basement as its own apartment, you will need proper zoning, permits, and a second exit per Chicago code.3.

They look a little different from traditional rentals: higher occupancy, often leased by an operator, and sometimes connected to certification programs or nonprofits.From what I’ve seen, the demand is strong, but the model comes with unique considerations: zoning, compliance, community relations, and specialized tenant management.I’m curious: Has anyone here explored sober living as part of their investing strategy? 

Get both the zoning map and the future zoning map. 

Hope to meet some friends and collaboraters here ( I feel I spelled that last word wrong, it's still in the red, but you know what i mean😂).

My custom new build was just completed, and I noticed that the 3 mini split units installed are set up as a multi-zone system connected to one condenser.

If medical collections are hurting the score, I have let that slide; if it's a utility collection like phone or electric, that is a red flag for sure. 

The best way I’ve found is to:Disclose as much as possible about the property and the borrower early onKeep communication open and consistent with the lenderPay attention to red flags—if a lender goes dark during the process or stops giving clear updates, that’s often a sign the deal is in troubleAt the end of the day, surprises still happen in this business, but having backup options and strong relationships with multiple lenders can make all the difference. 

not crazy, but need to look at zoning restrictions in the area you want to invest.