Since I have not gotten into investing yet or have never been in real estate full time I am a little short on recommendations but I would like to help you.  

My objective is to buy and hold for the next 10 - 15 years (my timeline is short).  

Long story short, the dad passed away, the mom moved on, and my friend stayed awhile but had personal issues and had to move away.

During this period I need to find a buyer.

I've seen other appraisals where a short sale was used as a comp, and it was indicated that it was a short sale, not an arms length transaction.  

This will involve actually knowing the city, or driving around those parts of town to become comfortable.3) Determine your holding period - if you want some quick equity, you can buy a place with some value add opportunities.

In my state of SC there is a year redemption period.

I haven't set my focus in the areas to invest in yet but I will be looking into the nearby markets such upstate NY, NJ and PA, once I settle my mind in this transitioning period. 

Lots of HOA problems, back dues owed, short sale, etc.

In short, you're going to have to test your market.