Nobody ever actually reads TAOCP*. Beyond that, you'd have to ask him.
Anything 'useful', or industry/professional related, are particular, specific things that he can get for himself, as and when necessary.
Anything 'meaningful', well, you'd have to figure that one out yourself - what would your son find to be meaningful? Certainly you don't think fun, or relaxation, or what he wants, holds any meaning for him. And certainly not reward. So you definitely don't think he should get the message that hard work actually pays off beyond being given more work to do, and tools that make him focus on work, because you think the only meaning of his life is to work, and that he shouldn't have fun except on your terms and when and how you allow.
He already has the objects he needs for professional development - a laptop. I'm sure he can figure out how to dual boot on it if he wants to dev on linux. Maybe the most meaningful thing you could do is let him make decisions - he'll never learn how to if you keep trying to control him just a little bit more.
*This is a(n obvious) generalism. I am aware some of us actually do go and read TAOCP - I have read some of it myself. I will profess that, on balance of probabilities, TAOCP will be a heavy and pointless shelf-weight if bought for OPs son.
Anything 'useful', or industry/professional related, are particular, specific things that he can get for himself, as and when necessary.
Anything 'meaningful', well, you'd have to figure that one out yourself - what would your son find to be meaningful? Certainly you don't think fun, or relaxation, or what he wants, holds any meaning for him. And certainly not reward. So you definitely don't think he should get the message that hard work actually pays off beyond being given more work to do, and tools that make him focus on work, because you think the only meaning of his life is to work, and that he shouldn't have fun except on your terms and when and how you allow.
He already has the objects he needs for professional development - a laptop. I'm sure he can figure out how to dual boot on it if he wants to dev on linux. Maybe the most meaningful thing you could do is let him make decisions - he'll never learn how to if you keep trying to control him just a little bit more.
*This is a(n obvious) generalism. I am aware some of us actually do go and read TAOCP - I have read some of it myself. I will profess that, on balance of probabilities, TAOCP will be a heavy and pointless shelf-weight if bought for OPs son.