With the holday coming up I would say it's time for dad to step in and let you get some sleep. Like tonight when he gets home you get to go to bed and he handles the bedtime and nighttime routine.
We co slept with the middle child for a few years. We didn't do it as much with the youngest cause he had what I call restless butt syndrome at about this age. For us a white noise machine was the answer because it kept his ears stimulated enough so that he could still sleep.
On those nights when he just wouldn't settle down we didn't give him anything to eat. I know nursing relaxes you both but you've created a habit and now he will have to be weaned from the habit. Substitute a pacifier or his thumb each time or if dad doesn't have to work the next day he gets up to do the rocking/sooting.
I would also suggest avoiding food then bed schedules but set a schedule. If you still find him going to sleep while nursing wake him up afterward to play before you put him in bed and let him go to sleep on his own instead of taking advantage of a sleeping baby and putting him down or napping yourself while snuggling.
if you're having trouble with him liking the crib then sleep with the sheet a few nights before you put it on his bed. The ambiant temperature in his room should be the same as in yours and so should the sleep wear and covers. Don't get into the bundling trap because he doesn't have your body heat to keep him warm. You've trained him to sleep one way and you have to stick with all those tricks except having mom and dad beside him.