The key is finding out what the seller wants as far as terms but the majority just want a quick close with the highest price. 

Don't see any major red flags here, so long as you are comfortable in the low income space.

That helped immensely and will be a major consideration for me!

I’m interested in value-add properties, but not to the extent where they’re in struggling neighborhoods, which is unfortunate because these areas are just blocks away from the major hospital.

My wife had to hand hold the majority of the interactions with the tenants and attorneys which was unacceptable.

I would pick a major tourist destination where it wasn't saturated with STR's already.That would take some research but you could google top vacation destinations and find a place you would go on vacation.

His listings were mostly on nystatemls but have begun creeping up on all the other major sites.One of the properties he listed is NOT for sale according to the owner and I suspect that to be the case for many others. 

The majority of my rentals I have acquired were for equity not cash flow.

Unless the property is in major disrepair, you are not going to have a problem in Florida. 

A lot of my clients are seeing great success in C/C+ locations that are in the major areas of growth, so they get the mix of appreciation and cash flow.