I am just so puzzled by your son! He is just no where near a typical 2 year old's routine, and I can't figure out why. He should have NO trouble making it to noon for a nap, even waking at 6:30 in the morning! The short naps are troubling, because even when you give him an early nap that nap is too short.
So, I'm wondering if you still haven't pushed nap late enough -- perhaps he's always UT at naps. Even a noon nap might be too early. If we got nap to be later, then we could get him into a decent bedtime.
The same with bedtime. You put him down so early that I think he's UT. Now, I realize you do this to avoid him being OT b/c he'll take 1.5 hours to fall asleep later too.
Are there any AP techniques that work for him? For instance, if you sat by his bed while he fell asleep, would it happen quicker? Here's what I'm wondering: can we get him out of this habit of 1.5 hours to fall asleep by using a little GW (gradual withdrawal) with you sitting by him to help him fall asleep and then we have you gradually move farther and farther away from him. I'm wondering if we can get him used to falling asleep at a more noraml bedtime (say 7) and within a reasonable amt of time (20-30 minutes) if that wouldn't break this weird sleeping phase he's in!
Because what you're doing now just isn't great for a family life at all. Plus, he's really not getting the sleep he needs either! So despite your best efforts he's not sleeping well AND it's disrupting family life. So let's just get radical and try something crazy, OK?
Here's what I want to do:
1) Let's try giving some medicine before nap just for the heck of it and see if that helps.
2) Let's make sure there's AT LEAST 5 hours A time between waking and nap. I want the nap to be no earlier than noon. If he's really struggling staying awake, try to keep him going with quiet activities in his room. Really push him. This kid sounds like he's very routine oriented, so I suspect some of the sleepiness you see is out of habit. He's on a 14 month old's routine right now! I think he's just used to it...
3) Let me know about how he does with you helping him go to sleep, if that works. If he responds well to you sitting next to him stroking him or whatever, we're going to do that for a couple of days to help him get to sleep faster. Then we'll do a normal GW series and have you slowly move away from the bed.
4) We're going to make sure that bedtime is 7 pm at the earliest. I know this gives you the heebie jeebies, but we really need to move him to a more normal routine. And I think for him a lot of this is just HABIT! But the problem is this habit isn't really meeting his sleep needs, so even though he's showing sleepy signs, he's still not getting the sleep he needs because the timing is off. So we're going to force the right timing on him and let his body adjust to it. It may take 2 weeks on this new routine for him to really start getting with the groove, but I think in the end he'll be much happier on this new routine.
How's that sound?