Aw, Jed. You can just about swing a dead cat in here without hitting the state borders. ;-)

Seems to me that if you maintain a note of respect and affection for your friend, his family will not take offense. If you've got that much material you might consider writing a BOOK about it, not just a song. It's certainly an interesting story about an interesting man. Stories about people choosing to drastically change their lives and pursue their dreams are always popular...This is something you could really sink your teeth into, if the family is willing.