Huge (((HUGS))) Honestly, I could have written your posts when DS was that age!! I was just so tired and frustrated all the time, and could never figure out what was going on! In retrospect, I think teeth were the number one problem, paired with OT issues, and followed by eating out of habit. I was BFing and he would always settle after feeding, but not because he was hungry, just that it was some sort of a prop for him. Ugh!! It was a very trying time!!
He is obviously OT but that might only be part of the problem, it does sound like discomfort as well. As for the bottle, does he usually take one at night? And do you think he was hungry? How is he eating during the day? Always gotta address any issue we can think of!
Definitely stick with shorter A's today, 2.5hrs sounds ok. Your naps yesterday both sounded OT, 30min wakeup were ALWAYS OT for us, and an OT first nap really does set you up for disaster in the afternoon, it's kind of a snowball effect.
Dare I say, if his am nap is really really crappy, don't be afraid to make that second A even shorter than 2.5hrs. It's a tough call, but sometimes drastic moves work when you wouldn't think so. You gotta think outside the box! My DS has seemed to be in strange OT loops lately, yesterday we went back to 2 naps and did 20mins in the am. Usually after that we would do 3.5hrs and then the pm nap, well he was obviously still tired and driving me nuts, so I put him down only 2hrs 40mins after his am nap and he napped for over 2hrs!! It's amazing that what you wouldn't think would work does work!! Don't pay attention to my nap and A times obviously as they're different because of the age, but my main point is that sometimes you just gotta try something different.
You said you tried meds last night after he woke up? Did you try them before bed too to see if it helped? I can't remember if it was this thread or another one that I was talking about pain meds. We also try homeopathy here - camilia or hylands teething tablets. They also help calm their minds when they got OT and can't settle. I know my ND recommended them when I was so frustrated and always seemed to be stuck in these OT and teething loops, and they really helped get past that crazy, can't settle, OT part.
Try not to get discouraged, this age is SO difficult to figure out!!! Hope you can get a nap in today.