Which ever city you go with I'd recommend looking into a local landlord association as they tend to have insider knowledge of all the rules and regulations.

Margins are thinner now than they were a few years ago, especially with insurance and cleaning costs up, but a strong product still wins.On the Florida coast, you get more variety — think smaller beach towns like New Smyrna, Cape Coral, or Anna Maria Island — less saturation but also more local regulation.

A lot of investors in that niche hang out in local STR meetups, regional REI groups, and even city-specific Facebook groups where hosts discuss regulations and openings.Curious — are you mainly seeing historic homes, or more rural/semi-rural properties with acreage?

First month is drawings, permits, and demoMonths 2-4 are construction: HVAC, plumbing, electrical, paint, trim, flooring, kitchens, baths, likely roof and exterior paint/sidingFinal week is punchlist, landscaping cleanup, listing prepComing soon to pending is typically about a week30 days to close

The flip is that all the counties to the south (those nearest WDW) are where a majority of the STR's currently reside due to more lax regulations on STR's.

The house is solid structurally and in a great area that I expect to appreciate, but I need to replace plumbing, electrical, add a bathroom, and paint the entire house inside and outside. 

Plumbing ground is put in and inspected / Cables and material for the slab are delivered around the same time5.

From an STR focused broker familiar with regulations and getting properties launched, top-tier investment focused lender, responsive title agent and capacity for boots on the ground (especially if out of state) any one of which can be the difference in succesful execution. 

I doubt that every single little repair ever made like replacing the faucets, etc. needs to be disclosed, I imagine this is limited to material repairs like major plumbing issues, structural issues, major modifications without a permit etc. 

All new plumbing and mostly new electrical and the stairs leading up to that unit is all brand new.