For insurance in South Florida, I’ve heard good things about companies like Citizens and some specialized providers that focus on high-risk areas.

Currently, I'm still buying, flipping, and running a PM company. 

There's little to no benefit to the owner and the person running the arbitrage is missing a very obvious, much simpler business opportunity- just start an STR management company and operate as such.

For the last couple of years I have been working from home for a very good company so I kept moving the financial goal posts because I wasn't miserable. 

These are self managed through my small STR management company.

Quote from @Rodney Davis: Has anyone done a deal with this company, Strategic Investments Partners? 

That's a terrible story about the Tesla but think about the guy who's running that company.

They tend to stay to themselves, not a lot of company or complaints. 

My main focus on Florida stems from an established working relationship with a property management company there.

These companies are fly by night hence why they don't buy their own properties...