Oh, we're finally planning on a "true" transition this/next week. Our son is 23mo's and we've had the crib up against the side of the bed (with one side removed) so it acts like a sidecar. Maybe you can start with that so it becomes just like an extension of your bed. We did that forever, then started talking to him- telling him how it was his special bed, with his own blankets, pillows, etc, and how we wanted him to sleep in it more often. He flops around when he sleeps so he'd roll into it, then roll out of it all night. Last week i started grabbing an extra pillow and waiting til after he rolled into the crib in his sleep, then i'd put the pillow between us. So far there's only been 2 times where he woke up enough and really wanted to nurse so he crawled over the pillow to me. Otherwise, it acted as a great barricade to his flopping, kicking feet and he never woke. Normally he'd nurse several more times in the night simply because he'd roll into me and that'd cue him. I'm thinking another few days of "pillowing" and we'll put the side rail on for the first time, see how that goes.

I hope that gives you some ideas. Good luck!