wake up 4:40am
E:7:00 am
A:
S: 9:50 (used to go down on his own but now must hold him til 80% sleepy...)
Do you mean that he's up from 4:40 to 9:50? I understand that you're trying to keep him on some sort of normal routine, but 5 hours of A time is most likely too much, which means that he's probably OT from being up so long (which is probably why he's having a hard time falling asleep).
A time at 10 months is usually at a max of 4 hours, so I might try putting him down closer to 8:40 and see if he goes down any easier for that first nap. You may also get a longer nap as well if he's not OT -- in addition, that might help you get a longer A time between your two naps.
I might look at some sample schedules (
chronological EASY samples, 10-12 months ) to see where other moms have been at with their A times and nap lengths at this age.
Right now, I'd work on that so you can get him caught up on sleep a little -- you're also at the age where LO's are starting to move to one nap (though not there by any means) --
10/11 month old sleep gone wonky? Read this first! -- so once you get him caught up on sleep some, you might want to look at doing a capped nap to keep your day shorter (and avoid those 4:40 wake ups)!
What do you think?