I'd say it depends on what the costs are. If he has to rack up a TON of student loan debt it may not make much sense. You can make friends and social connections outside of school if you create the environment to do that. Its a lot easier in school but to avoid the traps of student loan debt its probably better to continue making/creating software if thats the end goal.
You don't have to rack up student loan debt at MIT or any of the other elite colleges in America. If your family can't afford it then you'll get a ton of grants from their endowments (and work study to supplement). It's the next level down in colleges, especially at liberal arts schools, where students get stuck with the bills.
That your parents could theoretically afford to pay for college doesn't mean that they will pay for it. The usual rule is that parents are not obligated to pay anything for their children over the age of 18. Only in some divorce cases is the situation otherwise. Before you mention emancipation or a dependency override, check the requirements, they are quite difficult.
That may be the case now, but I graduated from Penn in 2006, and it was different story then (until about 2008 I think, with Princeton being the first to break the trend). Before that, a portion of your financial aid would be a loan directly from the school. My loan was subsequently sold to Citibank.
I would wager that MIT has some of the best return on capital in the world. MIT is an amazing school, has an amazing reputation, and getting an engineering degree from MIT will likely be worth it. Like was already said, the network and life experience are really amazing. I could only imagine the kind of people one meets at MIT. Interesting and intelligent people with similar interests.
I went to a coding school (I also attended university) and I would say that when you are young, college is an amazing experience where you learn a lot about life.
I think someone will eventually crack the code by getting a school together for 2 years with >500 students and partner with a university so that students can get social activities in. This, in my opinion, would be the absolute best scenario.
A college experience, amazing education, and a long enough time horizon to learn and build interesting things.
