I went through this myself, for myself. I grew up in south Texas and when I was graduating my friends were all making plans to go to Texas or aTm. I had the opportunity to play JUCO ball out in west Texas and I took it. The school was in the middle of nowhere and was the complete opposite of the big/ D1 college experience. While there I thought it was awful.
However, as my 50+ year old self looks back, I would not trade it for anything. I have lifelong friends from those days. And, yes, I often wonder how it would be if I made the other decision.
I guess my point is that he will have wonder/ regret with either decision. He will also remember fondly about the decision he did make. I think in the long run he wins either way.