That's a really tough one. 15-year-old me was basically a different person. Rage and love. Superiority complex: thought I was better than everyone and hated myself at the same time because of rejection from the in-crowd. I'm probably too hard on myself: I had a lot of the same values, just more twisted. I was trapped and felt like I had no control. I was kind when no one was watching, but had to put a show on in front of anyone to maintain the arrogant SOB facade I thought gave me character. The funny thing is that people who know me might be shocked to hear me say that because of how I masked around different folks but I know internally I've changed a lot.
Part of him would be surprised I didn't ctb by now, especially since I'm neither famous nor ultra-wealthy.
Luckily, he wouldn't give me shit for being a "wage-slave". That's more 22-25 year old me. (Well, more like 22-25 year old me would just kill themselves immediately knowing that nothing broke me out of the normal routine.)
15-year-old me would be mad I don't have more accomplishments or wealth.
He'd be excited that my wife is gorgeous, lol. I hope he'd be happy overall with the relationship. I see no reason why he wouldn't, but my younger self might be upset it isn't whoever I was latching onto that week or that she isn't more dark and edgy.
He'd be glad I moved away.
He'd be weirded out by the fact that I drink, but glad I keep it in check and don't have wild tendencies.
I like to think he'd be happy with my progress in guitar, and absolutely with my progress in songwriting/production, but he'd still be disappointed I haven't done anything professional with it.
The question is overall. . . He'd probably say out loud that he thought I turned out pretty okay but inside his pessimist ass would be devastated that my life is so normal.