I know here in Ohio my aunt got a quote to have her kitchen painted. She ended up with three quotes from some guys off of craigslist and the phone book. Her cheapest quote to paint the kitchen that was maybe 8' x 11' was $275. She knew I needed the money so she asked me to do it for her. I washed all the walls down really well to remove the built up crap from the 60 years the house has been around, removed all the doors that might have been painted accidentally. She also had me install a fan while I was there for her, and after two days of work, about 7 hours a day she paid me 400 dollars. I know its a little different with her being an aunt, but she had the extra money at the time, was helping me out, and she knows that a lot of effort was put into the room making it look very nice. If this guy is a true friend and you are able to help him out above and beyond the 50, and you know that the money above the 50 will really help out his family then pay him what you can. If you think it will get pissed away on something unnecessary then ask if you can pay a small bill for him, or go grocery shopping with his wife and help him that way. I know I would appreciate that too if I was him.