I missed this thread the first time around! In the pre-covid world, we went about 5-6x a year coming from the SF Bay Area. Our travel patterns were usually as follows
1. January -- long weekend (Fri-Mon)
PRO: cheap rates, relatively low crowds (once the holiday decorations are down)
CON: sometimes crummy weather, no holiday decorations
2. March -- Food & Wine festival (no kid on this trip), we've even done same-day FIFO (fly in 7am, fly out 11pm). Best to use a charter plane/semi-private to cut down on time at airport if you do that.
PRO: food! great weather
CON: variable attendance because of spring breaks
3. June -- longer weekend (Fri-Tuesday)
PRO: not yet hot, june gloom! love june gloom.
CON: schools are starting to get out, local APs not yet blocked out
4. September -- mid-week post Labor Day, 3 days
PRO: this place is just dead after Labor Day (relatively speaking)
CON: still hot as heck, no halloween decorations up
5. October -- Short weekend (Friday-Sunday)
PRO: Halloween!
CON: absolute worst crowd levels ever, like 9-10/10...almost as bad as Christmastime (thought we haven't been lately), weather still unsettled (we've been when there were Thunderstorms that required an emergency landing at the wrong airport, followed by extreme heat in the 90s + humidity).
6. November -- Long week (Sunday-Thursday encompassing Thanksgiving)
PRO: Holiday decorations, weather is pretty uniformly cool (no more 90+ degree days)
CON: it's fairly crowded
Total of 21 days in-park by my count, that's about $31/day if using a $649 flex pass not including any discounts the pass affords. Most of these stays are using off-site hotels, except our November trip is typically on DVC points, and we will occasionally book DLH or GCH if the stay is short in order to minimize transit time to/from the parks.