That said if you're looking at buying or converting into a multiunit, you should be able to at least break even with 2+ units if you're looking at doing mid-term (saw your other post).

Some other secrets are programs investors can use to save money on downpayments or to buy more properties without having to use income like Non/QM (DSCR or Bank statement programs). 

Or is it more advantageous to keep renting and buy an investment property to rent out instead?

The new breed of seller financed note buying trainers will teach you enough to find notes for them.

The best way to verify that is call the current agent for the policy and ask them what happens when you buy it - will the carrier still offer a policy?

Now I want to sell a handful of LTRs and buy another STR, this time preferably in Florida.

C properties have no ceiling fans, I will install for $50 if they want to buy it, but it stays at the end of lease, (unfortunately they are usually taken when they leave anyway).  

Is it possible to purchase a home from someone, and give them the first right of refusal to buy it back at a specific price at a later date?

Can locals afford to buy a property there for $100k?

My options usually include the all cash/quick close to flip myself, listing it (as an agent) but also offering the seller to do a JV flip together, I could wholesale it, offer to buy it myself for a BRRRR or other long term personal investment, etc.