Alright, we've created a bit of a monster with my son for naps. We do a bottle, rock and sing, and then sit in a chair near his crib until he falls asleep. Its been like this for months (he used to fall asleep while drinking the bottle so this is a transition from that bad habit).
Lately it is taking longer and longer to get him to fall asleep. Today I left after 50 minutes and he still wasn't asleep. I ended up going back up to give him some books to look at because he had stacked all the buddies and stuff in his crib and was jumping onto it. Now he is at least sitting quietly and looking at books.

I am committed to continuing to push naps, even though he certainly tries to skip them whenever he can. When he doesn't nap he's a mess from about 3:30/4:00 on. Yesterday he didn't nap because we were out and about, and he fell asleep at 5:40 for bed, the second I set him down in his crib. I also just think a 2 year old needs naps.

So. I should nap train? Like completely change the routine, get rid of the bottle, and just commit to doing it for a few weeks? How do you nap train a toddler? He was trying to climb out of his crib, but I flipped it around so the short end is up against the wall and that has stopped for now.

The other issue is that he does seem to take awhile to wind down, naturally. Like at bedtime he will just talk to himself and sing for 30 minutes to an hour.