I am also a teacher - you don't have to use your points in whole weeks - which was a big part of why we went with Disney rather than some of the other time shares where it is "Sunday through Saturday". We just don't vacation that way! There are plenty of long weekends, holidays, breaks.
Everyone has their own point of view. We bought into DVC more than 10 years ago and I don't think we have been back to the park since then, maybe once on the back end of a cruise. So, what do we do with our points? We often stay at Hilton Head or Vero Beach (husband & son go to baseball spring training every spring, daughter and I sometimes go down for long winter weekend to thaw out). We have done 3 cruises and would love to do another.
We have traded out a number of times - twice to Hawaii, the first time we tried to get tradeouts in Honolulu, on Maui and on Hawaii. Only 2 of them came through so we stayed in a hotel on Hawaii. They were beautiful. The second time, just hubby and I, we went to Maui and stayed at gorgeous Grand Wailea Resort. We have also stayed at $600/night (if we had been paying) hotel in New York for a long weekend. We've stayed in the Smokey Mountains, etc. You just have to get your request in early and hope it works.
My "screen name" is outdated now as older child is in grad school and younger a junior in college. One thing I'm looking forward to in the future is to be able to, when our kids are planning their weddings, to say "you can have 500 points to use wherever you want to go on your honeymoon". We have enough points that we hope someday to be able to host kids, spouses, grandkids on periodic vacations. Plus, we figure in another 20-25 years, we'll just split the points and give them to the kids.
We like the flexibility.