We live in Edmonton ("the land of snow and mosquitos"), and we've been buying annual passes since 2004. We go to
Disneyland every summer, and also throw in the occasional Christmas trip as well.
In the past, we've experimented with various strategies including renewing passes before they expire, but in recent years we've settled upon a strategy which involves buying passes every second year. To illustrate:
- our current passes were purchased the first week of August 2016, at the start of our summer vacation
- I just completed purchasing airfares and making hotel bookings for our next major trip in July 2017
- this year, we are also fitting in a five day Christmas trip the first week of January 2017,
We almost always buy Deluxe Passports which have a significant number of blackout dates, so we must take that into account when scheduling vacations. In particular: since our daughters are old enough that we don't like taking them out of school for a week, blackout dates often mean we can't always fit in a Christmas trip. This year, the stars aligned properly and we are going to Disneyland from Jan 3 to 7.
According to our long term plan, we will next purchase passes in August of 2018 and repeat the above process.
EDIT: I just wanted to add that one of my pet peeves is that, despite being Disneyland passholders for many of the past 12 years, I have never received a communication of any sort (snail mail, email, or phone call) from Disneyland regarding our passes. I assume this is because we are Canadian. As I understand it, passholders who live in the USA receive, at a minimum, yearly mailings when their passes are about to expire.