Hiya, I am not a Nap Mod, or Stacy but I am anyone - so I'll try to help you!
Does Emmett have reflux? I ask this because my son was diagnosed around 4 months. Before that he was ok, just farted alot. Here is a post about s/s of reflux:
https://babywhispererforums.com/index.php?topic=654.0 Reflux gets alot worse when teething happens - perhaps this is why you are seeing it now?
I think it would help us help you if you could post your exact routine - the one you follow, not the one you would like. Also, are you doing a wind down? Are there any props: paci, rocking, bouncing, feeding to sleep, swing - anything? Can you tell us exactly how you are doing p/s please?
At 4 months old, the 4 hour easy is ideal. Yes you can have sleep problems with naps and night wakings, and early wakings on the wrong easy as the A times are most often too short. I think perhaps moving to a 3.5 easy, and then to the 4 may be helpful, doing it slowly.
When napping is an issue, its best to not go by a usual A time. If baby only sleep for 20 mins out of a 1.5h nap - he isn't going to be able to handle a full A time next - your best bet is to feed, read a book, cuddle, change his diaper - then start winding down again - and try again to get him to sleep. Repeat this for each short nap/A time until you get to the catnap - then steal that nap anyway you can - Catnaps are freebies and you are 'allowed' to make them happen anyway that you can - car, swing, stroller, whatever.
If you want to still try wake to sleep - if the pressure method isn't working try the stirring - go in 10 mins before he usually wakes for a nap (this means he would have to be napping for the same length for a few days) stir him gently - until he moves slightly, and then I - duck to the floor for a few mins THEN leave. I found often times when I stirred and left - my leaving actually woke him up - maybe I am an OX - but waiting for a few after I stirred him helped it work better for me.
I hope this helps some. Perhaps a call to the doctor to rule out reflux or something else (ears?) my be in order? Are you medicating for the teeth pain? We love Hylands Teething Tabs is my house (ask your babys pedi before trying any new meds) and Tylenol. Motrin works best I feel - but Emmett is too young for that yet so stick with Tylenol.
Love and Hugs!
Zoey