@Dustin Pavlik
Yeah, incorporated St. Pete has a "30day min up to 3x per year" restriction, but if you search online you'll see Airbnb's all over Pinellas County. The city of st. pete is aware and considering sending out rules and restriction education to local residents, but since the address isn't shared before booking, and it adds more cost and resources to regulate, the city isn't proactively cracking down. Unless neighbors are complaining.. you're ok.
There are a few muni's in Pinellas that are STR friendly. Largo, Palm Harbor and more.
I recommend to clients getting into STRs in St Pete... analyze the deal and check the numbers as an STR... AND... MTR and LTR, or could you sell and make a profit as a worst case exit strategy. Margins are tough here in the St. Pete market but there is always a deal to be found.
You may want to plug in with a wholesaler or someone who has access to off-market deals for bigger discounts in PP to increase your margin spread.
$/sqft is still high here in the 'burg. I like to use this metric as one of the benchmarks for understanding whether a deal is terrible, ok, good, or amazing.
This and run it through Mashvisor and Wheelhouse for STR market data inputs to plug in to the analysis.