He's a skilled worker ... with no dependents ... living in your house ... you're covering all his needs, even his insurance and phone ... and he can't make ends meet? I don't believe it. You're making/accepting excuses about the tools, the car repair, his immaturity. He's a spoiled kid taking advantage of you, and changing that won't be easy:
- He needs to work more hours, or he needs a second job.
- Or, he needs to start selling some thing (i.e., video games) to raise some cash and pay off his debts; seeing things go out the door at pennies on the dollar could be a good lesson.
- He needs to pay more rent, not less. He needs to practice being an adult, not be coddled. Does he know you're saving the money? He shouldn't.
- Does he really need the car to go to work? Without it, what could he do? Take the bus? Ride a bike? Ask a friend for a ride? Note, I didn't say, What would he like to do? I said, What could he do? If he's not going to make his money stretch, he should get used to being creative.
- Does he really need a phone to go to work? I doubt it. If a phone were needed for his job, his employer would provide it.