We have been taking our kids out of school for one week every year. However, we won't in the future (this will be our last time this December). They will be entering the 3rd and 5th grade.
Once they leave elementary school, the homework gets heavy. Plus, the demand outside of school (swimming and dance) increase every year too.
Trust me, I hate conforming to the school schedule. I love Orlando in October and early November and late April-early May. The crowds are low and the temperature in nice.
That being said, we went to
Disneyland last August. It was really great. The crowds were not bad because it was the 2nd to last week. Los Angeles schools were already back, but our kids were going back the following week. Plus, the weather was simply fantastic.
I suggest trying to "game" either the first or last week of your school districts calendar compared to other districts. We live near Chicago. The first 2 weeks of June are great days to go downtown because the Chicago public schools are still in session.