My houses that I did cosmetic repairs on have been solid but I did not get my money out of these deals when done.

Personally, I would look to move out and buy a property that needs some cosmetic updating and rent yours out.

Interior designer for a light rehab, mostly cosmetic updating+ photographer 3.

Both of the lenders are correct Fannie Mae will not lend to "subject to" appraisals, which means if they house needs more than cosmetic work then that is out the door for a conventional loan.

The property has good potential as a Med Term Rental in the future, and minor cosmetic updates can be completed as tenants turn over to keep rents improving in a positive direction.

Delayed financing would not apply, you'd have to wait the standard 6 months.If the debt is secured by another house (cash out refi Property A to pay cash for Property B, for example), then it was a cash purchase, and you could do a delayed financing cash out refi in less than 6 months.Pragmatically: Between the labor issues and everything else, we aren't really seeing people actually put up ADUs, or complete major non-cosmetic renovation, in less than 6 months, anyways (everyone has a whimsical timeline where they think they will take 2-3 months), making it moot. 

These areas get high rents with cosmetics done.For southside Pilsen, Brighton Park and Bronzeville will still get good tenants and bit cheaper price points.These areas will get cashflow + appreciation + rent growth.

The extra 3k is for any cosmetic upgrades or repairs that I make to add some value although that isn't the main goal with this house hack.

I may need to add a new HVAC and maybe a few cosmetic things, but someone already lives in it so it can't be that bad!

If it works, and isn't causing a potential risk/hazard, then it's cosmetic and can wait.