Would you buy a neighbor's home who's facing hardships?

[Jerry Castillo]

A retired neighbor of mine in his mid-60's has been having financial issues for years, is now having health problems. He's mentioned to me recently that he wants to fix his house to sell as he's on a fixed income. I gave him the name of contractors I've worked with but he never called them, I'm thinking it's likely due to not having the funds to make repairs.

Neighbor's profile: Him being an open misogynist, he's managed to tick off all the wives on the street. He's got quite the large ego as well. All the neighbors have some stories on him. He is "that neighbor". Over the last 7 years he's become a recluse. Another neighbor who lives next to him, (when they were on friendlier terms) has been inside his house & said he is a hoarder. He only puts out recyclables on trash day, never seen a trash bin. He's a former sales manager. 

Neighbor's Property: ARV 330k, paid 195k in 2003. I haven't yet asked what is owed. Repairs TBD.

He considers me a friend since I was his only neighbor not to stop talking to him. I feel sorry for him as he lives alone & stays alone during the holidays. My gut tells me to pass because he's likely to get difficult when his ego steps in, but I like the challenge of this.

Hoping someone can suggest a win-win solution when it's a distressed (& difficult) seller who you've known for over 10 years.