I'm very glad that my mother, my best friend, and an uncle warned me ahead of time not to let my kids sleep in the bed with me. They all explained that it was great when you needed to nurse every two hours but what a nightmare when it came to converting to their own bed. I feel for you and I know plenty of others that have struggled just like yourself. My sister-in-law is due in July with her second child and needs to get her oldest to sleep in her own room. Not working well because papi can't stand to hear her cry.
Unfortunately I don't believe there are many things you can do to convince him outside of letting him cry a bit. I made the mistake of keeping my oldest in her bassinette by the bed until she could barely fit at seven months old. She was so use to being next to me, me patting her little bottom at every whimper, putting a pacifier in her mouth and nursing her even when she didn't cry...that she had a horrible time going into her crib and her own room.
I slept on the floor by the crib for a few days holding her little hand through the slats. That was super comfortable. :)
Finally I just got so tired I couldn't take it anymore and I tried a method I read about. I laid her down on her tummy, patted her bottom for a minute and then told her night night and walked out. I would let her cry for 15 minutes or so and then go back and lay her down, pat her bottom and tell her that it was night night time. I would leave the room for 15 minutes or so and then repeat. I never picked her up. I always laid her down and patted her bottom and left. It took about five times the first night. Then maybe three the second night and by the third and fourth night maybe just one or two times. After that I might have to go in once a week or so and do it one time, but she did start sleeping on her own. She still isn't great about getting herself back to sleep if she wakes up for whatever reason, but she does sleep in her own room no problems. She's five now and she has a three year old sister that never had any of those issues really. Don't know if she was just different or I just didn't make the same mistakes. I rarely have to go into her room for anything. She lays right down and is out in two minutes and sleeps all night. She's been doing that pretty much since she was a few weeks old. Just nursing at 7pm, again when I got home from work at 11:15pm...and then sleeping until 5am and back down until 7 or so. Can't complain.
Maybe pick him up when he's already asleep and put him in the crib. Lay him down and pat his bottom until he falls asleep. sit beside the crib and hold his hand until he falls asleep. But once he's in the crib don't pick him up. Pat his bottom, gently lay him down and sing. Shhhh him and keep laying him down. Don't pick him up.
I guess what I'm saying is you have to be more stubborn than he is or he will always know he can manipulate you into giving in. And when they are 16 that is not good.
Hope you can get something out of this post...and good luck!!! I know how it is to go without sleep. Most of us mommy's do. We all feel for you.