I have read this series of posts with great interest. I am a Webelos Den Leader with 11 boys in the Den. The total number of boys in the Pack is 20 (very small). 2 of the Webelos are in 5th grade, 1 is in his first year and the other (my son) is in his second. It is hard to balance the requirements the 2nd year Webelos need for AOL with the ones the boys need for their Webelos Badge. I planned on crossing my son over ASAP, but have since rethought it. Mostly based on maturity, but also would like him to cross over with the other 5th grade who will take longer to complete his requirements. I didn't plan on being the Webelos Den Leader, but the other one quit after the first meeting. I am glad I stepped up as this is my first time as the Den Leader (I have been an Assistant DL, Committee Member and Venture Crew Advisor in the past). I plan on 'crossing' over with my son when he goes, but part of me wanting to wait now it my loyalty to the boys in their first year.