I like them to always occur during the time of the in-game season where they make sense. It doesn’t matter to me what season it is IRL.
The biggest struggle I’ve had is with timing certain holidays. Because IRL Christmas and NYE are exactly one week apart, so I like that in the game, too. But then I have New Year’s Day on Day 1 of spring, when it’s really not even close to spring yet (only in my dreams in the Northeast US!) Then again, it doesn’t make sense to have the new year start on any day other than the 1st of something. And if I made it the 1st of winter, I couldn’t have Winterfest in winter. So I just deal with spring coming sooner.
