Is the market there hot? 

Would a hot tub be easier to maintain / more desirable?

https://www.phila.gov/CityPlanning/resources/Publi...pg 40/41"[1] When the proposed use is in an attached or semi-detached building, the household living use regulations of the residential district to which it is attached apply.

Maybe a super hot unit on South Beach or something in DC i'm emphatically confident will turn substantial appreciation in the very near further.

The article, mentions a household would need at least $114k to afford a median priced home ($420,000 as of writing).

Your goal with a property shouldn't be to hold it forever, it should be to build enough equity to use that to buy another or to sell when hot and turn it into two assets.

Currently readjusted my household cash flow to focus on debt reduction and cash savings that way I can invest within the next year or two.

INvestors would drop him like a hot potatoes.. so far that hasn't happened. 

Many of the older homes that haven't been renovated will not have insulation or HVAC, and will certainly be needed to be comfortable during our really hot summers.We ended up doing a BRRRR (Which we ended up selling due to the hot market a few years ago), and it was almost a complete gut, so I'd be happy to discuss numbers with you.

Clearwater and Tampa are hot STR markets for sure