Hi Krista
Just been reading back over your posts.... so how are things going now? Have the NWs reduced at all and have the days improved?
Reading back, I wonder if he may be really OT. So really keeping on top of those A times would be vital. It's really hard when LOs don't give tired signs until it's too late and their sleep window has closed (I think this may be what's happening) so what Sherry was saying about A times becomes really key. If you can find their 'perfect' A time, stick to that rather than waiting for signs.
I used to cut out certain toys and activities towards the end of Charles' A time so he had a chance to really cool off before WD and bed. Also, up until around 6 months (I think...

), I kept certain toys out of the room during the first A time - activity mats with toys dangling, flashing lights, noise. I found from experience that this helped. Also kept the first A time shorter than the rest As during the day simply because we got better naps this way. When the first nap goes well, usually puts you all on the right foot for the day.

How about jotting down your EASY (rough sketch!) and a little about your sleep routines: WD, sleep environment (white noise or music playing, dark room?, toys in crib?, easy sight of door etc).
Hugs & hugs
Charlotte