As someone who is motivated and has worked from 14 til now, 29 with only 10 months off (shut down my automotive shop due to the economy) I can say, this is THE BEST thing you can do. When I was 17, fresh outta high school, in junior college, working 3 jobs, 2 part time, one full time, I was stuck in a rut feeling like nothing was going anywhere, cuz it wasn't. Bus his ass down to you, show him how to maintain, change a flat, etc. Then make him SHOW you how to do it. And repeat til he has it right. Msf course, and hit the road. Say see ya, far enough away from home to make him have to work at getting home on the 500 bucks. That way he learns good spending habits etc. For me to get motivated, it took me getting sober and meeting my wife. I was 18 yrs old, and glad it came at the right time. I've sinced, bought a house, ran my own business, got married to her, lost my business, and coincedentally lost my house too. But I still go to work everyday, and am thankful that things are on the mend for us financially. Go for it. You're talkin maybe 4 grand total, in the grand scheme of life the money doesn't fucking matter, but the life lesson, could change the dudes world.