M.M.
I'm a big fan of varying versions of crying it out. We've tried several, as DS is now 2. And I have to say, it works every single time. So there's something to be said for that.
DS got into the habit of waking up and wanting his paci in the middle of the night. We turned into trained circus seals because it was just easier to go in for 30 seconds and pop it in his mouth, than to go the other route. But once we reached the point where he was waking up 3+ times/night, I hit my breaking point.
At 17 mos, we did CIO again. We had only 1 hard night, and he cried for 20 minutes (we watched him on the video monitor). He was fine, and it KILLED us to do that to him, but our sanity was in question. That was all we had to do to get our point across. We have had no issues since.
So, I know it's hard, but it usually works immediately. If you can battle through the crying episode, you'll be thankful in the end.