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.

Sometime/some places the insurer will approve the claim, as they don't want to be held responsible by the next owner insurance for roof claims (there is a legal term for that, my roofer told me about all this), so it's worth to look further into this approach.

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.

Is a title search as simple as approaching a title company to reseach the title?

Is there a cheaper streamlined approach to this or do we need to go through the whole probate filing and attorney hiring which I believe will be around 5K?

She is currently in there now and when she returns, I am going to approach her about this but I feel I need to be a little more calculated than normal.

We do lots of things but I am very picky about my approach.