I talked to a GC and ADU in general are fairly expensive to deploy these day even for a flat surface in the backyard.

Ill send you a DM :)Are you finding that the Tampa STRs are doing well even with the 7 night minimum ordinance?  

It’s hard because all I want is cash flow even if it’s $500 and hold for the appreciation. 

I literally couldn’t even make offers on 5 of the 7 houses I looked at last month.

Before that it was primary residence since January 2019.Do I need to sell it this October to avoid capital gains tax to qualify for 2 of last 5 years exemption for capital gains (up to 250K single, 500K married filing jointly)?

Like anything is sales (and you are in sales even when you are trying to buy a property), the less clean cut the deal, the more likely it is to get rejected.

Keep in mind that even with such a low LTV, you might not find anyone to lend above the UPB of the note. 

Nightly rates up and running at very low vacancy had a few months over 90% even where any little gaps get filled.

Cleveland, Ohio is a great market to focus on for cash flow and specific pockets have gone up 2x and upwards of 4x in the last 5-10 years even!

I've noticed in my area that houses that have been converted into 2 units tend to sit on the market for much longer and sell for much less than traditional single family houses with similar sqft and finishes.