I guess the reason I hesitate to move forward (and herein lies my question) is because he is a good friend. I trust him
completely, but I know that emotions can run high especially when money is involved. Have (or do) any of you ever
done this kind of business with a friend? My dad has some assets with a long-time family friend and I think it's been
pretty much a wash--nothing great, nothing terrible. My first concern is our friendship. Any thoughts and/or experiences
you can relate would be much appreciated.

I think the answer for both of you is no. You do not want to deal with a life long friend and he does not want to make a bad investment for a life long friend.