RE: Ok, is he too OLD for this stuff? Am I babying him?
I don't think you're babying him.
Crib - DS is 22 months and we're not planning on moving him out of the crib anytime soon. He has not tried to climb out of the crib yet. Personally, I'm not sure I'll be able to sleep knowing he's in a big boy bed and can just get out of bed and roam around whenever.
Highchair - We feed DS in 2 different places in our house so he uses a high chair in one place and a booster in the other place. I don't see any reason why you need to move him to a booster if he's happy in the high chair, not trying to get out, and still fits.
Rocking - If he's happy with snuggling, I'd say just continue it.
Potty training - We are nowhere near potty training!
Mommy to 2 DS's (2003 and 2007)