This structure probably just means more grey area which means more legal fees and perhaps less chance of either of us being covered at all.

No, he's not an architect, he drew all designs, floor plan, site plan, etc, and we had a structural engineer design his part, and paid an architect to sign off on them.  

@Preet Oberoi Purchasing a short-term rental (STR) or tiny home to offset W-2 income with depreciation can be effective if structured correctly.

Even duplexing down the first floor unit can be pricey as it involves making structural changes.

Shop around for debt to see what is available and model the various structures to see how the different terms impact performance.The tradeoffs will be fixed vs. floating rate, conventional vs bridge vs CMBS vs bank vs agency. 

Tax-Exempt Bonds: Tribes can issue tax-exempt bonds for certain types of developments, reducing financing costs.Challenges: Projects often need to be structured as joint ventures or leases with the tribe, and compliance with tribal laws and federal rules is critical.

RentRedi had no ability to manage this.  100 was the primary address of the property, which would show on google maps and such, and then 101 was an additional address that I legally owned and wanted to use (same structure).

While the cost can vary depending on the scope, zoning, and materials, I’ve seen similar projects run anywhere from $50,000 to $150,000, depending on factors like plumbing, electrical upgrades, and structural work.If you’d like, I can connect you with a few contractors or architects in Chicago who specialize in basement conversions.

Luckily I did have a clause where the sober living company is paying all repairs and maintenance unless it is structural issues.

This will not qualify for 1031 Exchange treatment under the present structure and "use."