Another teacher here! I'm from TX, and we don't have any equivalent of "New Jersey week", nor do we get Presidents' Week off. I'd feel sorry for myself, except I do get 9 days each year - 5 from the state and 4 from my district. They are not picky about how we use them, as long as they are not adjacent to a school holiday, which is kinda stinky. Our secretary has told us that if we MUST take a day next to a holiday, we can be docked, or call in "sick." They really do not raise eyebrows unless you try to take more than 5 days off in a row. Several teachers from my campus took 3-5 day trips last year.
I don't feel guilty taking off - still, it is a LOT of work to be gone that long, and then there is "catch-up" when you get back. Before I went back to teaching, we would take our young kids out of school to go to WDW in the fall. We also USED to have a fall break, but they have taken that away now.
We joined DVC in 2006, right after I went back to work. DH couldn't wait to plan a trip - being our first, we went to OKW in January (the very lowest points possible). I took off 5 days, and had a fantastic time, but coming back was a killer for me. Since then we have learned that going in the summer is hotter, yes, but we can stay longer and relax more (and we have bought more points, so aren't as chintzy about weekends). Being from TX, the summer heat in Florida is really not that bad.
We have gone in July and June, Christmas, and are going this year for Thanksgiving! Christmas was crowded, but we weren't trying to do everything - just wanted to soak up the Christmas spirit. Those times were so much more relaxing to me in the long run than that January trip. Crowds are low in January, but park hours are shorter, more attractions are closed, and we have discovered that is a big month for training new employees. We used to swear we'd never go to WDW in the summer, and it is now my favorite time to go!
I did take two days off this spring to take my youngest daughter to Disney - it was our "turn" for a parent-child trip, and it was totally worth it. A weekend for the whole family is more work than I want, but this was perfect for the two of us - priceless memories, and she wrote a trip report for her 1st grade class that they all loved!