I think I'll have a dedicated spot for the seasons, like a small display area I can easily change out 4 times a year. I feel like if I had to change the whole town it would be kinda overwhelming.
I plan on switching out the entire decor based on the season, if I can. That being said, in New Leaf I burnt out after a few months and didn't even make it to fall, then on subsequent playthroughs I only played in spring, so it hasn't been since City Folk that I've messed around in winter or fall.