As for inactive characters: When they come back, they begin taking actions in the current season. They don't get any special "pocket-time" to catch up, because it's assumed there character was up to something the entire time (though that something is probably, like, wenching and drinking at the local tavern or otherwise resting and not doing anything important/useful).
I probably wouldn't do that simply because: What if they were in the middle of combat? Or maybe in the middle of some important dialogue? I'd let people finish with that, then skip ahead.
No, no.
It's like...you can only travel so much in a season. Once you run out of travel time, you simply can't travel anymore until the next season. You can continue to act, though.
Well, acting would take time too, but of course, not nearly as much as traveling. So you could continue acting for a good while, in case you are ahead of everyone else. But you would still hit the "Wall" in time Eventually.
Perhaps month changing could be based on votes as well, so once the majority of players want to move on, those behind
have to skip ahead.
If you do have to skip ahead though, I guess that actually would be a good excuse for some traveling, so you actually use that potentially lost time.
Which is why I suggested Game of Thrones seasons. They allegedly last for years, so movement could be made less restrictive.
Could you explain this a little more in depth? How exactly would that work out?