2) Where are his friends at: the Webelos I den or Webelos II den.
3) IS HE READY FOR BOY SCOUTS IN 6-9 MONTHS?!?!?!?!?! (caps for emphasis)
My middle son was in a similar situation last year. Originally he decided to skip Webelos I and go straight into Web II since he would have been eligible to Crossover in May. He eventually decided he wanted to remain with his friends, and will be Crossing Over in December with his den.
I want to emphasize the last question because it is VITAL. We had 4 Scouts from 3 different packs cross over early. 1 Scout had no issues as that pack begins the Webelos to Scout transition as soon as they become Webelos in June between 3rd and 4th grades. They also have a year round program. 1 Scout had some initial issues as that pack really incorporates the Patrol Method after December of 4th Grade Year.
The issue was the last two. Their pack did NOT begin the transition process until the Scouts actually crossed over. They were very ill prepared for Boy Scouts, and held back their patrol to the point that the patrol was abolished and the patrols were rearranged after them being in the troop a year. They are FINALLY getting their act together.
Eagle94-A1's post in Skipping Webelos I was marked as the answer