Since he has owned each property for a number or years, it seems that his long-term strategy has been to cut corners and avoid capital expenditures, betting on appreciation in the end.It seems to me that two of his parcels in particular would be excellent candidates to be torn down and replaced with high-end apartments or condos; the same thing is happening across the street with another, much nicer (but much larger) multifamily property.2, The second person Currently, I am building a mentor-mentee relationship with a local investor who has fix-and-flipped over 200 properties.

These chinese shops that pop around every city is a good bet with pricing on quartz.

In fact, I would bet that they somehow blame you in this situation.  

Your best bet is to contact an MAI appraiser in your area and ask for a feasibility study as to the highest and best use.It's not always up to you from a market aspect, unless you build it. 

@Dion DePaoli  the forgiveness of debt is many times over looked in these deals.and I bet the person who stands to make a bunch of dough is not giving the person who has no clue tax advice and or could really give a rip :). 

I would bet this is section 8 housing.That being said, this zip code is appreciating quickly.Next to our house (which is about 1/2 mile down the street from the property you are considering )is a 2 unit brand new condo that sold for $350k per unit in Seprtember.  

You just do not scream "trustworthy, and safe bet" with a hand written letter in red ink on a yellow piece of paper torn off a yellow notebook... 

You can't renovate a house, and you can't discern a property value, which means you can't evaluate a deal.What you have a ton of, I'd bet, is time.

Anybody want to place bets as to whether they were gone or not?

If he is solely in it for the monthly cash flow aspect, out-of-state is going to be his better bet.