... rather than leave it to one of my buddies who might get me in some sort of trouble.
What's the fun in that?
Okemo is like a family resort and attracts lots of those types. Killington is more mixed and has some better night life. Either way, if you go to Killington, stay in Killington proper, not Rutland.
Killington terrain also beats Okemo but Okemo has its charms. Since some of your friends don't ride at all, I think you're going to want to do Killington.