Oh what a shame, so frustrating when you think you've finally cracked something and then it all goes downhill again
Definitely sounds worth trying the resettle without a feed again, you might want to try feeding around 5ish if he wakes then another night, if only in the hope of getting a later WU, if that's what you want?
I'd really struggle with giving up chocolate, especially when so tired
Is there anything else that you'd enjoy as a substitute? Not sure about the pressing face into the mattress thing - I'd just be concerned that it means he's rolling and if so shouldn't still be in the swaddle? Or do you mean he's rubbing the side of his face into the mattress whilst on his back? If so, it's possible that could be self soothing - some LOs have some funny ways of self soothing, I seem to remember DD at one time would lift her legs right up and crash them down again, this was actually a sign she was starting to soothe herself! Later on she'd suck on the bottom corner of her sleeping bag by stretching her feet right up by her mouth - would be pretty uncomfortable for me
but seemed to work for her
I know it may not seem like self soothing just yet, especially if it doesn't end up being successful for him, but he'll eventually find something that works for him...
Keep posting a day's routine now and again if you want fresh eyes on it
Could you perhaps APOP a longer nap to help him get over his OT?