Boots are easy, go to Aspen and pay a little extra to have the liner custom fit. Store bought boots ride like a Ford Escort, custom liners ride like a Ferrari....the difference is night and day, best money I've ever spent.
I have a pair of skis I'm selling with bindings, they're essentially "new". They were a gift and I only went down the hill a couple times on them and hung 'em up. If he's anything like me and wants something completely different that no one else has, then these are it, 2013 Amplid Syntax 172's(Austrian company) that are drilled dead center, I don't remember the exact bindings right now, they're not top of the line but not cheapies either. They are a park ski, super light and setup as such. I'm selling for $300 if you're interested.
But just go to Aspen with your son, they are pretty helpful.