J.D.
Every child is going to be "off" when you start a new chapter in their life. Since he will probably be more active in the preschool, pick him up with snack and drink in hand. That really made a difference in my sons behavior. Also - don't feel bad for putting him down for a "second nap" - if he's tired/whiny - then he needs more rest :) LOTS of kids don't sleep in a group setting, one is whining, one is giggling, the other tapping, and MOST of the time the teachers just gab away and wisp around cleaning etc. while the kids are supposed to be napping! Good luck - Synopsis : pick him up with a snack and give him a nap :)