They caused me to lose the cleaning fee on numerous bookings (45 of them) within a matter of weeks.

Find some Multi-family (5 units or more) Not to be a wet blanket but you might find other discussions of FL law on this site interesting.

After listening to numerous experts they have suggested, for newbies, to focus on one niche & strategy and master it before expanding to others.

Most of us are just getting our beaks wet and trying to learn the process and develop the capital to eventually scale to your level.

If the goal is owning numerous properties you need to buy accordingly.

@Sharlene Burch - Do you have any opportunities to rent the assets you already own to get your feet wet and see if you like landlording?

Additionally during this time I had 2 HVAC unit repairs, an electrical repair, 2 water issues in basements, a property that was flagged by Code Enforcement as uninhabitable due to a tenant's trash, a broken garage door, roach infestation, clogged plumbing, a broken sliding glass door, and numerous other items!

Buy a small MF and then rent it out at first to get your feet wet, and then once you get the hang of it, and if your market supports that location making a good STR.

Between the networking and numerous resources, you can gain a lot of insight from BP. 

The guideline from Fannie/Freddie is 6 months, but numerous lenders would make borrowers wait 12 months before they could use a new appraisal amount for cash out.