).We have ALWAYS gotten what we wanted.
I don't think we have ever been waitlisted for anything. In my signautre, you can see where & when we have visited.
Btw, I'm a teacher too (I've never let that stop me from a half-dozen January & early May trips).
How do you get those January and May trips in?

If you are happy staying at your home resort, don't need a specialty option (concierge, 3 BR) and book day one 11 months out willing to accept any unit type in your size, your chances of success are going to be almost 100% unless there's a fluke situation like the Summer Olympics come to Orlando. If you add the WL at the time of the call if it's not available, your chances of success increase further. While those times you mention are slower than some, they are not as slow as the rest of WDW for the same dates. Realize that it's no only possible, but some would say likely, that both of those times could increase in the number of points required to reserve, esp Jan.during booking. I see a lot of people get wait listed. I understand during the busy time, but what about the off seasons. We travel during fall breaks. If we purchase DVC, we would start trying to go the first 2 week of June, or 2nd week of January. I am a teacher so my times are limited.
I've always used my personal & sick days. Sometimes the person at my school in charge of Payroll would find "creative" ways to record my "personal" & "sick" days if it were one of my longer trips. Sometimes we'd go to WDW for about 6 or 7 school days.
It also helps to have a school with several staff members who take vacations during the school year.
My district is VERY strict about Personal and Sick days. And we can't use either before or after a weekend with a day off already. So Jersey week my wife and kids can go the whole week, but I have to work all three days. So I'll end up arriving after them, or changing weeks we go.I couldnt get a standard view studio at blt for dec 7, called yesterday at exactly 9. Only need 1 night before a cruise.
My waitlist came through this morning.