First day of vacation, first day of sleep training

Yesterday was my first day of Christmas vacation, and also my first night of trying sleep training with Cooper. I never had to do much actual "sleep training" with my other boys. It was mostly wait until they slept through the night, which they did well on their own. Cooper is still up 2-3 times a night and Friday night was up 5-6 times. I've been so tired I've been falling asleep nursing in my chair the last few nights. He's been sleeping in the antique cradle in our room, but only has about 2 inches of room at the end when he's lying down and really has outgrown it. I feel bad that Tony hears every time Coop fusses and I get up, the squeaky chair I nurse in, the burps, belches, and squawks.
Sleep training? you ask! Right now I'm trying to get Cooper to sleep regularly in his crib. I'm hoping that the distance from me will give him more time to wake up and me more time to think about if he is really awake. Part of the waking up problem is that Cooper won't wake up completely to nurse and will just nurse a little bit. He doesn't want to burp after eating at night either. This makes him wake up an hour after eating to burp or spit up, which wakes me up. I've been really bad too about bringing Cooper to bed with me to snuggle and nurse. He LOVES snuggles and eats well snuggled up, but doesn't nurse so he is fussing just a little bit later.
Cooper slept both naps yesterday and most of last night in his crib. He slept a good two hour nap today and he's asleep in the crib now. I'm hoping if he can get used to sleeping upstairs then I can put the cradle away and move my nursing chair into Coop's room. It is a pain to go up stairs to get Cooper back to sleep, but I'm hoping we can slowly work from 3 times a night to one time a night by January 3rd when I go back to school. I would dearly love to be getting more sleep and longer stretches of it.
I'm not a fan of the "Cry It Out" method, though I did get to a point when I did it with my other boys. Maybe it's because Cooper's my third baby, but I've had more patience with him than ever with the other two. I haven't had to have Coop cry for an extended amount of time. I have been becoming more and more frustrated with the late sleepless nights recently though. Hopefully having two weeks off work and some time to sleep in and get naps will be a good time to get Cooper scheduled and get me some more sleep.