It sounds like the alcohol contributed to your hypochondria

[edit] lighten up, for the love of god. I'm taking the downvotes on principle here.

He "often wonders"? Seriously, he should get over it - there's nothing he can do about it at this point, and he's admittedly a highly functional person at an intellectually demanding job.

[2nd edit] Here's a desnarkified version of my original comment:

Life is hard, and you're going to screw some things up, but you compound those mistakes by focusing on what you could have been rather than what you could still potentially be.