For me the the CFA track made the most sense because equity/commodity markets interest me, but find your own, create a plan, and don't pick your head up until you find yourself where you saw yourself in the beginning.

I'd also toss in that you want to take a more active role in the community and that him selling this to you give you that chance.Sounds to me like this guy is going to value time and sense of community over dollars and cents...

The difference between the appraisal and the listing is 1,200 additional sq ft.The house is priced at a multiple that makes sense for the original square footage listed given the area, but applying that same multiple (or even a decent bit lower) to the appraiser's higher estimated size would get a significantly higher value.Could a buyer be sitting on a windfall that the seller missed?

If that makes sense..

Unless of course they are part of the deal, i.e. they are the boots on the ground/sweat equity and you are the finance part of the team, then it makes sense. 

All in all, to answer your question, if you have done jobs with your guys before, you can bargain with them for good prices, always get 4-5 estimates per job and make sure that you are getting a price that makes sense.

I don't know if any of this would make sense or cash flow since we don't know any specifics about market value, established rents, etc.

Would it make sense for me to approach him about doing a Warranty or Quit Claim deed to get him out of the mortgage and I take over the payments and ownership of the home and prevent him from foreclosure?

@Antoine Martel - That makes perfect sense...I setup searches for Buyers all the time- so I will definitely do this.  

Economy is strong, resilient and the sense of community for such a large city is second to none.