So glad to have come across this thread.... We are headed to WDW 8/20-8/30. It happens to coincide with a move we are making to Colorado on 8/8. My DS 8 is entering third grade. Colorado is school of choice, and they have quite a few charter schools. DS is on a wait list for one we really like that starts 9/2... So he wouldn't miss any school.... However if he doesn't get in to this school he will have to go to the neighborhood school which starts 8/14! Therefore he would miss the first two weeks. My DH and I stressed about going on trip in case he has to go to neighborhood school. Ultimately we decided that he will need a celebration trip after our big move across the country. We want to make this a positive thing for him. So we decided to book knowing there is always a chance he will be missing school. In the end, he's a good student, and we believe family time is very important. We will catch him up if need be. I agree that school districts sometimes cross boundaries by telling families what they have to do with their children. There needs to be some sort of balance.