I am also curious about when/how an attorney/legal involvement comes into play with this.

Play it smart by aligning your investments with your goals, timing, and risk appetite.

Leaves an immediate bad impression.Entry Door: This seems silly but make sure your front door opens and closes easily without the need to play around with the door. 

Others noted that the appreciation play could make it worth keeping, I tend to look more heavily on appreciation since real estate investing is more of a long term game.

Vrbo and Airbnb do not play around when they see you taking direct bookings from guests who found you through their platforms. 

Negotiating felt like a game of chess—except I was playing against a grandmaster, and my queen was missing.

There’s demand for rentals in the area, and multi-family properties tend to hold value even in market shifts.New Construction: With SWFL growing fast, new construction is a big play, especially if you can tap into neighborhoods where demand is rising but inventory is still limited.

@Brady Ascheman To make the decision strictly from a Property Management standpoint you have to calculate your vacancy cost and cost to acquire a new tenant to know if a rental increase is even a smart play. 

FHA is unlikely to play nice in this situation.Bank statement loans might be an option for you.

Also wonder how appreciation plays out in that area as well.