I manage about 40 STR's in Pinellas County and the area you are outlining is a good performance area, with the right property of course. 

If this is an investment property that's leased and performing, DSCR cashout is probably the simplest path. 

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – so, they often select the first PMC they call or that calls them back!

If you do fall within either, you are permitted to ask if an animal is a service animal, and (if it is not obvious) what task(s) it has been trained to perform.

@Shyam Subramanyan Yes, you can perform a cost segregation study on your STR properties for the 2023 tax year, even for properties acquired in 2018, 2021, and 2022.

If you perform a 1031 exchange, you may avoid immediate recapture taxes, but long-term holding strategies must account for eventual recapture.4.

Doing this like a brrrr I see as the best bet, for example my property does still have room for improvement adding a bedroom and bath to the primary structure and then the ADU.

Highlighting the STR revenue potential, especially in a prime location, could attract investors looking for both income and future appreciation.Steps to take:Prepare a detailed financial breakdown of the property's current performance and future projections.Include comparables in the area to show both STR potential and anticipated appreciation.Offer flexibility in the buyout terms (e.g., structuring it as an installment plan if needed).If you can’t find an individual investor, you might look for a property management company or real estate investor group that specializes in STRs.

The safest bet is to try to get a variance from Union City. though clever, your combined unit lease agreement would likely cause trouble if ever scrutinized by the Tenants or the municipality. 

I think the outskirts are you best bets!