SteveC
Doing the best imitation of myself
I think this is a really good point. It comes from the fact that if the heroes keep winning, what is there left to do? Eventually you "win" and things genuinely do get better for everyone, at least in a game where characters reach the power to affect things on a global level. I think of Pathfinder's world, since that's what I'm running. If you've played Wrath of the Righteous (I've played the Video Game) or Kingmaker (ditto on the Video game) you end up making HUGE changes to the world. I guess another big bad just has to come along and start to wreck things in order to have another group of zero to hero adventurers fix it.Ravenloft may consistently reset itself, but so does Forgotten Realms. So does Greyhawk, whose default state is to perpetually be on the brink of war. So does Eberron. In fact, we want these things set in these unmoving states and when designers have tried to advanced timelines and materially change the tone of the setting, they generally are not well received as in the case of the Greyhawk Wars, or the various catastrophes that hit Forgotten Realms and are eventually undone.
I think eventually you get to a deconstructionist game where you take that into account. Since I'm thinking about Ravenloft, I'll recommend Puffin Forest's Ravenloft campaign. In it, Strahd realizes that whatever happens, he's going to come back, the Mists are going to come back, and ... it's all going to start over again. He hatches a plan to change it.
I think that you can either just accept that a game has a starting point and start all of your games there, or take what happens into account and have the world really change. The problem with that second idea is that what comes next may not be nearly as interesting as what it used to be.