When he does go down, how long does he nap for?
An hour or two at a time. He starts getting tired at 8 30am-ish if I take him to bed right away he is usually asleep by 10 sometimes as late as 11. Today he woke up from his nap at 12 15 and was rubbing his eyes again at 1.
I just don't know if he can handle it, the longer I stretch it out the harder it is to get him to sleep.