This has crossed my mind a good deal, as it’s something I’m trying to work into my systems. Ever since Ars Magica showed up and used the march of seasons to regulate Magus training and rate of adventuring, I’ve been enamored of the idea. Pendragons winter didn’t quite affect me the same way. I’m happy to see more systems adopting regular use of long time periods as components of play.
I’ve never taken a close look at Bastionland because the premise doesn’t interest me, so learning about it in discussions is my only exposure to the system. This aspect, seasons changing, I find interesting. Not to the point where I’m going to buy the system, yet I’d love to hear more discussion on how the seasons advancing affects play.
I have yet to get the game back to the table. But were I to get it back at the table, I would absolutely advance the clock; probably not the season but to the next event for certain.
My thought is that these time skips are useful when significant time has passed since the last session.