Hi S.,
If you want him to sleep through and fall asleep by himself, let him cry until he falls asleep. My 16 months old daughter was never a good sleeper either, but I jusr couldn't handle being up all the time, especially being pregnant again.
It was very hard to get through, but once done it all is so much better.
There are different methods. There is a book out by Dr. Ferber you can read his mnethod is a more gentle one, he strectches the cry time every couple of days.
I couldn't do that so we went ahead cold turkey. We did it a lot earlier than you guys though. When my daughter was 6 almost seven months old and still came every 3 hours we started the crying it out process. It took almost a week, but ever since then she sleeps through the night, okay, unless she is sick or so of course.
The first few nights are the hardest. We rung with don't go in all night long. We were more exhausted than ever before because ithurts you psycologically so bad too.
The truth is, the baby is fine, they don't die from crying if they are older than 3 months, they just fall asleep after that much crying at some point. Your problem is, you waited very long so the crying will be very very long too. Be prepared to hear him cry for hours if you want to accomplish your goal.
At 6 months, Maja cried falling asleep and a couple times throughout the night. The first falling asleep was a 2.5 hour stretch of cryiong followed by a 1.5 hour in the middle of the night and a 45 minutes again later. THese times reduced every night, till she finally went to bed after a week without or just a couple of minutes crying at the beginning of the night and then she slept through. Now she goes happily to bed and sleeps through most of the night.
We put white noise in her room, that helps her a lot and we bought ourselfs some earplugs. You can still hear them with the earplug, but it is less loud, makes it alittle easier.
Good luck with whatever you guys decide to do.
T..