At our doctor’s urging, we just got around to forcing Moishe to sleep in his crib all night. There was a modicum of crying, but not what you’d expect. Our actions won’t have him in therapy for years during teenagehood, nor will he have abandonment issues because he had to sleep alone.
I think the child-raising industry really makes this one more difficult than it really is with the competing theories about how to handle it ("cry it out" vs. "let them move at their own speed"). Our anticipation of the separation anxiety was much worse than the actual event. In the end he cried just about as much as he normally does in a night (three times for a total of about 45-50 minutes).
Our night, on the other hand, was wonderful. I haven’t had the bed to just Sarah and I for over a year now. Though we both slept restlessly, it was nice to get a whole night of sleep.