Need Bumpie motivation, help, inspiration...whatever!

Ok so in preparation for #2's arrival (in January) we have made DS1 a new "big boy" room complete with a big boy bed.  He loves his bbb...he gets in it and lays down like he is going to fall asleep, he loves to snuggle in it..etc.  

The problem is when I think that it might be the right time to try it out for good and I turn off the lights he freaks (I have night lights plugged in too) Mind you the room is no where as dark as his current room.  I know when the time comes I will snuggle with him until he falls asleep to get him going per se.  I will also make sure he has all of his comfort things from the crib.

I guess my issue is when should I bite the bullet and make him sleep in the bed?  I think it will only take a time or two before he is comfortable...he is pretty easy going.  Do I go cold turkey and once he sleeps in the bbb never go back to the crib?

tia