...and judging from some of the posts on here, I'm not the only one!

DS is ten weeks old, and while he's not a horrible night sleeper, his naps are pretty brief, 30 minutes tops. I'm trying the every 2 hour rule (and reading HSHHC) since looking for sleepy cues doesn't seem to work for us, but after seeing some posts on here about moms who are able to put their DCs down for naps before they are fully asleep, I am worried. DS really doesn't fall asleep on his own (except for the stroller, and an occasional catnap in his bouncy or swing, but that is less and less frequent the more interested in his surroundings he becomes). So when the 2 hour mark hits (or earlier if he's really obviously tired), I swaddle him, walk him and/or rock him, sing to him, he usually cries for a bit, and I do this whole routine until he is completely asleep, gently place him in his crib, and tiptoe out of the room. If he isn't completely asleep, he wakes up and we start the whole routine again. So I spend 20 minutes soothing him to sleep, and 20 minutes after that he is back up! Chat Icon ANd I KNOW he must be overtired.
So my question for the BTDT mommies is--if you are able to put your DC down for a nap before they are fully asleep, HOW did you do that? Did you do it from birth? Are we setting ourselves up for an inevitable CIO situation once he is old enough to do CIO? I know right now we can't spoil him, but I fear we are definitely headed into bad habit territory walking/rocking him to sleep every time he goes down, but I don't know what else to do...
Also, I think he wants to suck when we are doing this soothing routine, but he won't really take the paci (at most he'll let it sit in his mouth, LOL). I am afraid to let him nurse himself to sleep because then I'll be the only one who can get him to sleep! Thoughts on whether we can get him to take the paci? He does suck on his fingers, but since he is swaddled for sleep, he can't...

TIA!