But given the future development right next door I'm not sure if it would be better to sell (take the money and run) or rent it out (pull out the equity to buy more real estate, cashflow a few hundred/month, and hope the building next door doesn't drop the value of my condo). 

VRBO doesn’t work any harder to process our payments, but they are getting a lot more money than they are from less expensive rentals.  

Anyone can give you a contract, but it doesn't mean it would hold up in court if you ever get there.And all real estate is local - each state is different - so you need to be attending local investor meetings to learn what to do and not do in your area.

Doesn't matter for tax purposes.

I’m pretty clueless on this side but that’s my understanding so let me know if it doesn’t make sense or you need other info.Appreciate all the help...

Or, if he really wants the property and is looking for ways he can afford it, he could again sit down and write out questions he doesn’t have the answers to that are preventing any action at all:1) what’s the property worth now as is?

I think if the kitchen pieces works with each other then it doesn't mater what it is. 

My mortgage on it went from 170K to 125K over the 12 years, it doesn't cashflow great, but when the mortgage is paid off I will cashflow 13K a year from it for the rest of my life. 

The title company doesn't seem to be as familiar with these types of transactions.

@Sherrod Mcgowan-greenOne that pays and doesn’t trash the place !