The problem is that it seems that it will be very difficult to generate even a neutral cash flow given the high HOA fees, taxes, and insurance in Florida.

I'm 51, been a corporate drone for most of my career, but made a leap of faith about two years ago and launched a small but growing tent and event rental business as a side gig.

Speaking as both an investor and realtor based in FtL, these small MF are very difficult to get into at the moment due to excessively high pricing leading to negative cashflow if you plan to finance them. 

So yes, I'd say the first step is to informally talk with the tenants face to face and get a sense of who will be cooperative and who could be difficult, and let that inform your strategy for each of them going forward.

OOS investing is much more difficult than advertised. 

It is difficult to maintain, it scratches, it warps, it stains, it needs to be cleaned with cleaners made for wood floors, pets tear it up, it transfers noise, it shows wear patterns, etc. 

However, I have a feeling they might be hesitant to provide one.Since this is my first out of state investment, I'd likely walk away if the tenant turns out to be difficult.

DO you have a day job that makes this even more difficult?

I have read LLC's are not the best to buy real estate with it being difficult to get loans from banks due the limited liability. should I put these properties under my name, or should create some sort of corporation/llc to put my properties under. 

To do a clean BRRRR in today's interest rate and highly competitive environment is very difficult.