Jenn, my plan was not to move him for as long as possible!
Then when he was teething his 2yr molars we got some bedtime resistance, and being too tired to deal with it we just took his mattress out and let him sleep on the floor, which he liked (about 23mos). Did that for a few weeks to get a feel for how he did, then converted his toddler bed. Around 24mos my dad bought him a BBB and he's been in it ever since. We made a big deal of going to pick up the bed and pick out his sheets and comforter (TBH, I don't think T really cared, he just wanted to run around the store!) He does great in his bed. We were having some bedtime issues for awhile, but they weren't directly related to the bed, so once we worked through them he started going to sleep in there like a charm. He almost never gets out, even when he wakes he calls for us to come get him! I'm waiting for the day when he tries to get out of the room.
I consider ourselves lucky that he made the transition with no problems, I always figured that once T was in a bed he's always get out, but he doesn't. Yet.