Any advice???

@Trevor Fleck Good advice comparing real estate to stocks as far as managing one's portfolio.

These comments are not legal 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?

Real estate investing demands ongoing education and flexibility, so stay up-to-date, have patience, and ask for advice from seasoned investors or experts when necessary. 

Good luck to all of youJennifer, with all due respect, when experienced investors give you advice and you call it "negativity" because it's not what you want to hear.