The post above makes perfect sense, not just because of its author.
This year I have started planning our winter getaway particularly early. Last December I was able to score J (mixed and full on return) for 25k Aeroplan points each way from YEG to CUN. Nothing even close this year. Maybe it's too early?
Wound up booking YEG - SXM for 17k in Economy early December, although the schedule can easily change. Then on local island airlines to PTP, then to Miami (AA w/ Avios) and back to Edmonton with Air Canada (12.6k). So some decent redemptions before school is out, but on a handful of dates. Been eyeing PTP and FDF for a few years, and it's always been a bit of a challenge as AC flies only out of YUL, but starting mid-December, I don't see anything particularly well-priced to the Caribbean.
My biggest worry, in addition to schedule changes, is new/updated vaccine mandates this fall. No one in our family will be "up to date" at that time.