I think it's awesome that you are being so supportive, though I could imagine your concern with money for college being an issue. It sounds like you live nearby to the school so maybe rent wont be an issue. Having gone to art school, I can say while it's great to get that degree and all, the best opportunity that art school presents is the motivation to practice and develop your portfolio. It seems like in the art world your portfolio is what talks and not as much the degrees that you have. Try lots of things and see what styles fit you as an artist. It might take a few classes to see that you really love working with oil paints, or illustration is your thing. Figuring out how to make that work in a tattoo setting will be his unique challenge. It sounds like he's got all the support he needs and that he will do great!
This is awesome! Great job on the shadows and lighting. Sometimes that's the hardest part to get right, without that realism goes out the window. The only thing I would play around with is the background, it looks great but I wonder what it would look like if it were a little more faded/darker so that the girl stands out more?