How flexible is your timeline?
When I first leveled up a character on my server, I was right in with the first of the rush. I was L60 at the same time most of the "first generation" were hitting L60, and so it was natural to assume that most people were at the same point in their timeline — they'd taken down the Defias at the same time I had, visited the Scarlet Monastery at the same time I had, went to Scholomance at the same time I did, and so on.
Not so clear-cut these days! With new alts being rolled all the time, events that are brand-new to one character are things I did four or five years ago with one of mine. How do you deal with a character who's just found out that the Scarlet Crusade is being run by demons? "Oh, I've known that for years." "…*splutter* You could have told me before I went in there." Or is the news new to you again every time you hear it?
The more interesting question I'm thinking about right now is whether it's feasible to juggle a timeline somewhat — could a character of mine level up to 60, 70, even 80, without ever tackling some of the quests that should come up at 30, 40, 50? In RP/IC, could I get a character out to the Argent Tournament before she finishes the Wrathgate storyline?
Even WoW itself does some bending, folding, spindling, and mutilating to give people the opportunity to do the same quests without necessarily being at the same point in the story. Take Drakuru — if you've done his Grizzly Hills/Drak'Tharon Keep quests, you get one quest when you see him in Zul'Drak. If you haven't, you get a different one. Either way, though, you have the same goals, and people questing together can definitely work together on them.
As NaNo approaches and I hammer down some of the details in Nancie's life, I find myself pondering what order she might have taken things in. There are some quests she probably would have avoided at all costs when she was supposed to do them, but that would make perfect sense for her character now. But it's a pretty twisty timeline, the likes of which might get me a visit from the Office of Temporal Affairs, and I'm hesitant to go for it if it seems too jarring. The fact that my character could have skipped past things, that they'd make sense for her now in a way they wouldn't have then, doesn't necessarily mean it makes good game-and-RP sense to put the timeline in a weird and unexpected order.