Forgot to mention... it takes him that long to fall asleep but we KNOW he is tired. For example, last night he slept 7-8 hours at most, and today he woke up from his nap after 30 minutes (OT for sure). We tried to get him to sleep again… it took us 3 hours or so.

His "routine" is quite inconsistent these days. Yesterday:
E: 7:30am (had managed to fall asleep almost 10PM the previous night... very late)
S: 9:30am (slept for 2 hours)
E: 11:30am
S: 1:30PM (slept for 1.5 hours)
E: 3: 30pm
S: 5:00pm (30 min catnap)
S: Put on the crib at 6pm (expecting 30 min to fall asleep), fell asleep only at 9PM!! After that, had frequent wakings all night.
Today:
E: 5am (woke up hungry since previous day he did not eat well)
S: 7am - 7:30am
E: 8:30am
We placed him in the crib around 8:45, since we realized for sure he would be OT from the terrible night, but he did not fall asleep.
E: 11:30am (We actually fed him again even BEFORE he ever was able to nap at all, gave him a bath, and placed him right back to his crib. Poor thing, seems to spend all his day there.)
S: 12:45 - 1:45 pm (we KNOW he was OT, but would NOT fall asleep until this time)
E: 3PM
And now, I've been in the room with him for half an hour... still won't sleep. That's where we are so far. Pretty hectic day

THANKS FOR YOUR HELP!!