Long story, but he lost his mom a few years ago and was in foreclosure when an investor approached him to save their home. 

If so, you have engaged in an ad homenim approach.

Glad you brought up this topic because this is the avenue I was hoping to go!

One thing not brought up yet is it may be difficult for you to get insurance on the home with the roof in it's current condition. 

A couple months ago they held a financial literacy type thing where they brought in a local banker to talk about personal finance.I was the only person who showed up.

I have done my due diligence and have brought in an inspector as well as my contractor who quoted 75K in repair costs.

It wasn't until I brought the 2nd guy in that I found out that the roof wasn't done properly, the framing wasn't done properly, and some other things that caused some rework. 

I appreciate the information, regarding approaching meet ups with caution.

That is true, but then again depending on how approachable and kind you are to the person when speaking to them it could change their previous assumptions on stereotyping real estate investors.Basically, what’s the worst that could happen?

If so, maybe she can approach them and get a big group together and spend some money advertising a common open house with raffle.