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if the kid is clearly one of the better players or dominant in HS his first 2 years, move on to a prep or JR team if that's what the kid wants to do.
However, the kid better be a very good/dominant player to even have a chance of playing in college. If not, that's ok as well. Stay in HS, enjoy it, have fun.
If you try to force it and make it happen and the kids really not that good, you're just going to spend a lot of money chasing your tail.