Yeah Jack is a little cuddlebug too. For bedtime the only thing I think we started doing differently was being more consistent. So for naps he goes straight in the crib with his aquarium toy on, and for bedtime I make sure he has had a lot of food, and then I hold him in the glider chair in his room until he rests his head on my shoulder and doesn't squirm at all. Then when he is asleep or almost there, I put him down. Books say don't hold them until they are asleep, but if I do he sttn! So the books can go suck it

He usually wakes up when I lay him down, puts his hands underneath him (he sleeps on his hands), turns his head and goes to sleep. Then last night when he started fussing at 10pm, I didn't rush in to nurse him. Surprise surprise, he made it just fine to morning. I actually think he is a pretty good sleeper, we just get inconsistent sometimes and I think his teeth were bothering him with teething. So it is like I was doing everything wrong. I hope it holds up! These babies seem to not like to be too good for too long, LOL.
It does sound like Dustin is on the right track! I don't think Jack is all the way there with self soothing a all, I think he is just tired.