So I better go check with the city.

This includes verifying income stability, rental history, and conducting background checks as permitted by law.

Check your state to see how long the PM has to notify the tenant of damages (some it is 30 days and you don't want to leave it that late).For damage to floors (or other things that have a limited life span), it is based on depreciated costs for replacement. 

Based on the Insurance Market in FL now, you may want to check on both options.Those policies are designed to provide Property and Liability coverage together.  

Also, I would check out Airdna to analyze the properties you are evaluating as a STR. 

HI Kev, we helped a lot of luxury STR investors this year utilize the accelerated deprecation tax incentive, I would actually suggest checking out the bigger pockets featured tax preparer section and sine it's likely a considerable reduction definitely not try and do it yourself..the investment in high quality reliable tax advice is essential to any investor tool kit. 

The first big check box is finding that property sweet spot.

Check out Simon Sinek’s video. https://www.youtube.com/watch?

There is a local group of individuals that gets together regularly, though, WI REI or something like that?  

Look at small multifamily homes with high rent potential and get a regular loan to skip PMI.