I would let him go for both weeks. Cooperstown will be the best time he has ever had! Perfect weather,atmosphere,setting and fields.All of the family, fans and umpires are so relaxed and having so much fun it was a great time.The players were tight at the beginning of the week but were loose after a few games.Our team sounds about as talented as yours and we played our best ball. Ended up the #1 seed out of 80 I think & finished in 3rd place! Va. Xtreme July of 2004.We,as a family, have yet to top that week!The advice I would give : Save your arms. Don't warm up as long, especially early in the week when the kids are ready to go.We had to tie them down(lol) or just don't get to your field too early.Send a "scout" to the field to make sure the game ahead of you is on time.Also have parents check out the teams you are playing to gauge talent.When we got our schedule I had a blast running around trying to see who had what,hit what threw what,etc..Not sure how much I helped the coach,but had a lot of fun! Then you can save your best arms for when they are needed.The week we were there there were aprox.10 elite teams ,20 very bad teams and the rest of us.Enjoy yourselves and be sure to take it all in as they grow up fast.