I've been talking to a realtor they connected me with in Clearwater, and they are a STR investor and own 10 rentals in the market as well as know the STR regulations street by street.

Agreed but Sole Prop will accomplish this without all the hoops you're talking about.

But I might pick something else if I knew what we were talking about here.  

She'd be happy to talk to you Ike!

I'd be happy to talk through the strengths and weaknesses with you.

Start networking with local agents and investors for insights, and talk to a lender to get pre-approved to understand your budget.

I’ve had the talk with him about what needs to be done before searching for another house.

If your local market is very active and homes are selling fast, you may be able to get by with doing less.Your Home’s Condition: If your home is vacant or has a unique layout, using a professional stager who can bring in the right furniture and accessories may help buyers truly visualize its full potential.Your Budget: Talk to your agent to get an idea of staging costs in your area, as it can be the difference between your house selling and sitting.

Let's talk about it.

If you are organized enough to forsee hang ups and talk with your GC about potential challenges on a regular basis, two brains are better than one.