I will take less profit in a hotter area that sells faster than gambling on a small town/slow area with "potential" for higher profits.  

I'd look into the states bordering FL first, then look into hot cities and go from there

I don’t know the person, but I would think you could afford to gamble $525.

Better to accept today's rates over waiting and gambling on lower rates in 2023. 

Short term rental is always a larger gamble with more headaches than a long term rental.

However, we were basically gambling on every transaction at this point in our career.

@Steve Vaughan  agreed very slippery slope... we all hear about Hewlit and Packard starting in a garage with 15k of credit cards in the early days... and well look where they ended up.. so who knows.. but it sure is a gamble.

IMHO,  whats important is to walk the property, otherwise, you are taking a vegas gamble with not being able to see the inside. 

Every time a tenant moved out 3 out of 8 evictions or so, it felt like a gamble, with someone leaving the place in ruins. 

It is extremely difficult -- bordering on practically impossible -- to use a 1031 exchange to move gains from the sale of one of your existing properties into a property that you already own.