I'm talking to a real estate lawyer tomorrow for some guidance, but in the meantime I'd really appreciate any advice about this situation, as I'm completely confused about what to do here.  

One piece of advice, even though they are not full towns purpose built for STRs.

Any advice???

If you're asking for free advice from a stranger on the internet, I'd encourage you to find a different STR market unless you want to have a place in Kissimmee for personal use.

Any tips/advices/insights are greatly appreciated! 

That said, any advice on which insurance carrier/broker i should reach out to get my rentals insured before May 1st? 

I believe this is very important since if a guest can afford a 5-bedroom pool home in the same neighborhood as your 3-bedroom home with a pool, most likely, the 5-bedroom home will book first.This is why I am reaching out for advice.

I'm getting started in the real estate investing world and am almost ready to buy my first rental.I’m debating between two different investment strategies and would love to hear advice from experienced investors here.Would you a) buy a two unit and house hack with 5% down (all cash in around 40k) in an appreciating area with a little bit of cash flow every month or b) start BRRRR strategy right away out-of-state in a C neighborhood.And a third option, if you have the ability to do both concurrently, which one would you start with first?

In addition to the good advice posted above, the two biggest flags I've come across:1.

I am based out of Cleveland, if you ever need advice on the area, I would be happy to help.