Not sure what lesson I learned as flakey board did not reveal itself for several days after install. 

If I ever decide to leave my corporate job I would consider flipping on the side as a way to keep my network fresh and generate cash for investments.Ultimately, investing is using money to get more time (freedom) and flipping is using time to get more money.

Offer to pay his move (with a max price) and  maybe offer him a 1k  to start fresh (only with the comdition that you successfully acquire the property).

Joe's brother-in-law buying Joe's house at a short sale would be a huge red flag for fraud.I think the biggest arrow in your quiver is #1, and your most probable path to success is to order a fresh appraisal with a fresh opinion of value, and once it comes back go to your (or the end-lender's) appraisal department (not the AMC, the lender's internal folks) and argue that the new appraisal is more credible than the previous one because of #1 ("if the appraiser didn't even go to the comps for a quick drive-by photo, who knows what else he didn't even actually do?")

These appraisals should reveal both an opinion of value, and let you know ahead of time if you will have issues selling and/or refinancing them.

If he moves out and leaves damage to the property, a fresh coat of paint won't help you too much.Personally, I'd treat "Joe the Painter" completely independently from "Joe the Tenant".  

Rent out your nice, freshly remodeled house for $1400. 

He told me that a local community bank (wasn't willing to reveal which bank it was) in Atlanta metro area allowed him to use his free and clear single family properties as collateral for multi-family financing.

There are openings in the upper west exterior walls where electrical conduit was removed.10.The stucco in these areas has not been repaired to prevent moisture penetration and deterioration.11.The front unit has issues flushing the toilet, which was confirmed with a tenant, so camera scoping of the drain pipes was performed that revealed damages and blockages in the pipes.12.Deferred maintenance on multiple items: cracks around windows and pipes, gas pipes are not supported, pilot lights in heater units were not lit, a water heater unit has no ventilation.I hired a plumber to scope the pipes (please see his report in the invoice attached and photos); a roofing company was hired to assess the damage to the roof above the middle unit only (please see proposed work sheet); a general contractor has inspected the settlement of the wall in the second unit due to the damaged frame.

But, typically I've noticed many of the residential buyers base their purchase on their needs and can let their emotions get the best of them.Both require you to act in the best interest of your client, but there is much more black and white on the commercial side where numbers really drive investment sales pricing and can be influenced by micro and macro economic factors.If I were fresh out of college and living at home I'd get started on the commercial sales side.