The game-generated Hot and Cold outfits can look weird sometimes, so it's probably best to change the worst ones. I've went quickly in CAS with each household to change these.
I plan on doing 28 weeks seasons, but since I don't have exactly 16 households in my rotation, it will most likely shift a bit each year. I initially wanted to one year per rotation, but I didn't realize new year's eve would fall in the middle of winter, and it kinda throws off my plan.
One thing I've noticed so far is that while visiting the family in other neighborhoods, there can be different weather there, which adds another reason to go visit them instead of inviting.