HELP - What would you do? Is this a Conflict of Interest?

[Jonathan Bombaci]

This is the situation: I have a family friend that is going through a bankruptcy. He needs about $100k cash to get clear of everything and he has a fully paid off house that needs a new roof but is worth $470,000. He approached me about selling it to an investor for $350,000 with an agreement to lease it back to him at $2500 a month for 3 years while he waits out the waiting list for senior housing. My thought would be someone buys it cash for $350,000 puts a new roof on it and the refinances it for $400,000 and takes most of their money out. I ran the numbers below, these are my questions:

1. Do you think an investor would do this deal? It's negative cash flow for 3 years but with a big payoff when they sell it. 
2. What should I worry about to protect my family friend from the investor after closing?
3. What would need to be in place to protect the investor from my family friend when the 3 year lease back is up?
4. I would do this deal myself but i'm afraid of the perception of a conflict of interest. I don't want friends or family to think I took advantage of a family friend during a time of need. 
5. Even if I just introduce the investor is the perception of a conflict of interest be something I should be concerned about? 

Thank you in advance to anyone that can provide some perspective to me.

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*This link comes directly from our calculators, based on information input by the member who posted.