I don't know what your son is like........
I am a Web 2 Den Leader of a den of two boys. With just two of them, the boys completed most of the requirements for crossing over into Boy Scouts last year, as well as most for the Arrow of Light. The troop that they decided to cross over into invited them on a campout last summer. What an eye opener!! Up until that point, I considered letting them join the Boy Scouts early. However, I really saw how immature they were when they were on the campout. Neither boy was quite ready for the increase in responsibility and teenage comraderie. They had a great time but the differences were very obvious to us parents. I backed off and slowed down abit for their Web 2 year. I worked on getting them to be the leaders' helpers for training and prep. of the Web 1s for the Webelos Jamboree and Webelos Woods campoouts.
Scouts is SO MUCH MORE than going outdoors............obviously, the decision is your son's to make. But don't taint his thinking by feeding into the "we can do it all at home" attitude. You can't. If you try to, it will be your son's loss.........