We flew with our son for the first time when he was 12 1/2 months, connecting flights from Houston to LAX. As each flight began to back up from the gate, I gave him a small dose of Tylenol to help him stay relaxed. To my surprise he slept the entire flights.
He had already given up the pacifier by then, so we didn't have that. He was already off formula. From Dallas to LA he did wake up and the flight attendant gave us milk for his bottle when we asked for it. On the way home, they would let us have it, said it was reserved for the 1st class. We got apple juice instead. Big mistake. On the flight from Dallas back to Houston, he had apple juice runs out his diaper and on to my leg. We changed him on his changing mat on our laps and put clean clothes on him. I always carried some plastic bags in his diaper bag, so that is what I put his clothes in. It wasn't much on my leg, I was able to use some wipes to wipe it clean enough.
As far as regulations, you don't have to have any documentation for him. But we did take his birth certificate with us. You can go to www.tsa.gov for the full regulations as to what you can carry on-board, liquid formula, powder, etc.
Do the pre-boarding if it is offered. That way you can get settled before everyone starts piling on.
If you have an umbrella stroller you could take it, because typically the planes have a small closet to put things in. I would not take a large stroller because they will drop it down for baggage and it might not make it to you at the destination. If you have a sling or pack to carry him, I would do that.
Check as much as possible. You don't want to have to carry your baby and haul around a bunch of luggage.
Will someone have a car seat/baby carrier for you to use once you get there? If you take his, they will drop it down to baggage for the flights as well.
As for the hotel, I wouldn't waste money on a special travel crib. Get some extra pillows and place around him. He should move around too much to push them off and fall off the bed. Is there a family member at the destination that has a pack and play you could borrow?
Go to the airport early. You don't want to be rushed. Just stay calm. Good luck!