I haven't read through all the posts, but just going through your initial post, I'd help him. Good friends are worth more than the money you'd spend. Especially if he saved your life on a number of occasions. Things are tight now, but economic history and time always shows that times and family monetary situations get better if one applies themselves. My wife and I were dirt poor when we got our house and have up and times over and over again. Still survivng, still got our house. We may not being high on the hog, but we have the essentials. Just remind the wife that you wouldn't around at all if it weren't for your friend.