Last week we tried letting the LP "cry it out" for brief times in his crib. The idea is that you get a set bedtime and a specific routine going, and after all the routine you put him in bed and leave for 5 minutes or so, and then you come back just to remind him you are there and you haven't left, but he has to go to sleep now, and you leave again. The time gets longer, up to maybe half an hour. We thought the LP was old enough now to know that if we say goodnight and leave, we are really still in the area and everything will be fine. (He's older than one would typically start the "cry it out" because of several reasons. Two of them are that I thought he would learn on his own eventually, and that we haven't really had the time/energy to commit to it--it's important to try it for real and establish a clear routine.) I think he knows that we are still in the area, but he does not know that everything will be fine, and he did not learn that after a week of trying. The first night, LP cried a lot but fell asleep in about an hour total. The second and third nights were a bit better. I still let him nurse in the middle of the night, then I kept him in bed with us, because I certainly didn't have another hour to devote to the crying process in the middle of the night, and I don't think that would be good for the LP either.
Then the LP kept doing worse every night. It was really sad to come try to pat him and calm him down, because he would grab our clothes and try to get us to pick him up, and he would panic again when we left. Two nights ago, he wasn't crying as much but was yelling periodically while waiting for us to come back. I think the longest we were gone was about a half hour. It may have been more because I thought he was sleeping--then I heard him crying again, and when I looked in, he was standing there staring at the door. He eventually went to bed after maybe 2 hours total. It really wasn't working, and it was making him terrified of bedtime. I can't say if it would have worked in another few weeks, but we were not willing to find out and risk that it got worse instead.
Last night, before bed, we decided we were done and he could come sleep with us, but we would keep the routine and work on him sleeping in his own bed on the floor next to ours. LP didn't know that of course, so he was in a bad mood as soon as we started the bedtime routine. When TE got to the last page of his book (the last step before bed), he started crying. He was screaming as I took him to the bedroom, but as soon as we laid down in our bed and he realized he wasn't going to the crib, he calmed down and went right to sleep, much faster than he usually did before the crying it out. Maybe the experience helped him figure out how to sleep a bit better overall, but we're all glad it's over.
P.S. LP's last cuspid has poked through the gums!