Having been a Den leader myself I totally understand you position. There is a part of me that doesn’t want to have these kids grow up too fast. There is another part of me the sees the changing world and how much more information these kids are taking in at much earlier ages.
The Webelos Program is really about 1 year and a half if a Pack takes the summer off. That means the Webelos 2 (AOL Den) is only together about 6 months or so if meeting resume in say August and they earn the Arrow of Light and can crossover is early as Jan or February. I know some packs to keep them longer but I’m speaking of eligibility to crossover. Since the Webelos 2 time is designed to basically begin visiting Troop meetings and integrating into the Boy Scouts I feel that essentially taking 6 months out of the program and getting them into a Troop would be something to consider. In fact the Arrow of Light Scouting Adventure, which is the final “pin” to earn the Arrow of Light is mostly the requirements to earn the “Scout Rank” in Boy Scouts.
Of course the boys are young when they cross over. That’s why the formation of a new scout patrol to keep the den together with a solid Troop Guide ( or 2) the be that go-to person to teach them the ropes and to keep the bigger and older Scouts at proper distance to speed up the integration is essential to making the transition. As each new Scout matures, and they will at different speeds, can be transitioned into regular patrols when it’s decided they can handle the move up.
Not every idea or thought is a good one, but keeping the discussion up is hopefully a good nugget can be found and used.