First, get as organized as possible and present yourself as a business, even if it's just you running a business.

I do however know a few people that have scaled up STR businesses here, like one friend/client who has 12 and there are some bigger players for sure.

Those are ownership stakes in the business that owns the property, not ownership in the property itself.

I’m thinking this would make a bit of sense for me since it’s a busy market (I think) and it’s only a 45 minute flight from my location.

I originally thought it would be an issue and provided streaming Charter but when I would ask after stays I was always told either no one bothered watching TV at all (too busy at the parks, etc) or they all had their own streaming services already and didn't need any.

I use Quicken for my personal finances and to see balances in business bank accounts.All my rental and expense stuff I keep in Excel.

This would be DSCR based product (no tax returns or DTI needed) but keep in mind business purpose loans in Florida can only be made to an entity (LLC or Corp). 

I find you just get a better education and experience if you are a busy realtor for stuff on the investment side. 

I know I have been busy thus far. 

Of course late payers aren't ideal but that's why they're renters and not owners, it's going to happen in the business but if there's no communication then that's concerning.