Honestly, I think I'd try him in his big boy bed now! But that's just me. I would think if he did fine this weekend, then he may surprise you. My dd is also spirited and I thought she'd never stay in a big girl bed, but she's only gotten out twice and I think she probably would've skipped those naps anyway (family in town and too hyped up). She's been in her big girl bed for a few months now and still sleeping like she used to. You could always try it and then go back to the crib if you need to maybe. I'm just thinking getting him used to the big boy bed in his familiar surroundings might be better and he might start climbing out before May and then you'll be stuck with both the transition to the big boy bed and the move and won't get to decide that yourself. We started potty training and the next day dd climbed out of her crib. Thought she'd do it all at once I guess. If you don't want to go ahead and do it, then I'd probably let him stay in his crib for awhile in the new house. The move might be enough of a transition for him to handle...