Thank you! I will check out the support thread for sleep regression. I think that's probably part of it, but I also think that with our holiday travels he got into some bad habits and that's building together to create a sleep problem. I will try to answer all your questions - so this may be a bit lengthy. Also since we've only been back home for four nights I will post what's happened since returning but also what happened prior to traveling as I *assume* we could get back to that.
Being this upset by the crib has been for a couple of months now. I'm the only one that can put him down. I wait until he's fast asleep and then gently transfer. There was a brief moment in time that he would go in drowsy but that was so long ago. Also I used to be able to put him down and rub his back, but those days are over. With anyone else putting him down he will wail as soon as they try to transfer him. So my husband simply wont put him to bed unless I'm at my wits end, and our babysitter (twice per week) will just let him sleep on her (not good.)
For teething we gave him Motrin last night but it didnt seem to help. He fought sleep for 2.5 hours while I held and rocked him. He tried everything to not go to sleep - first he was hungry, then wanted another book, then wanted milk, wanted to bang on my chest, pet my hair, yadda yadda. I could see his eyes getting heavy and then he'd pounce awake and have a burst of energy. Sweet boy did give me lots of hugs and kisses

Then of course he was awake from 1-3:30am, and then woke this morning at 6:30. Ugh.
While we were on vacation for 11 days, his BT was all over the place. I simply had too much family and we had too many events to try to get him in bed early. I did make sure that he got an hour nap in the AM and an hour nap in the PM so that he'd get some decent sleep.
Before traveling his schedule was roughly like this:
4:30-5:30AM Wake (yes this is crazy early and a problem in itself)
Btwn 7:30-8:30 Start morning nap for 40-60 minutes (used to always be an hour but lately was self waking at 40 minutes)
Around 1-2pm Start afternoon nap for 45-60 minutes
Around 6:30-7pm Start bedtime. We were doing earlier for awhile and it was hit or miss on if it helped him sleep longer. Tried later a few times and that was also hit or miss.
Up until recently he has been a happy go-lucky kid, so I always felt like he was getting the sleep he needed (even if it wasn't great for us to have him wake so early). But the past several weeks he's been more clingy and needy during the day. He is such a snuggler, he just wants to be picked up, held and loved on. I love that about him but have noticed a change in his neediness during the day (as well as separation anxiety has increased as well.)
Like I mentioned he always had pretty good mood during the day so I didnt sweat being on a strict schedule, and felt like he was getting the sleep he needed. But now it doesnt' feel that way anymore and frankly we are exhausted with his sleep issues - taking hours to go to sleep, waking for up to 2-3 hours in the middle of the night, and then EMW.... and all at the same time, he must be exhausted! I am hopeful the middle of the night waking is due to teething and traveling issues, but then we're still left with a circus act to get him to sleep and waking at an ungodly hour.
Thanks so much. Sorry that was a novel!