In general, you want such a lengthy endeavor to have some sort of payoff; some resolution to a current conflict. You also want some way to record it! Break out the chat logs and screenshots, or you'll be kicking yourself later. And if this is a true resolution, make certain all involved parties are on board with the possible outcomes. Or just wing it because you trust your partner. ('Hey, we should probably have some consequences for this. Let me do a /roll')
The Lunar Festival has come and gone, and thanks to some very bossy people my shaman now has the Elder title. Don't tell said bossy people, but I actually had a pretty fun time doing this. Oh, I still hate the fact that you have to spend hours upon hours just running from place to place, and while waiting for Wintergrasp to be Horde controlled again Saturday night was fairly epic, it was also epicly annoying. What made it tolerable was (1) doing it with a friend and (2) having an in-character reason for all the running about.
I'll confess, I'm probably never going to get the violet proto drake, even though I've now officially done all of the meta achievements. Problem is, they're scattered across four different characters. While Elder is hard-earned for my shaman, it would be laughable on my deathknight, and the same is true for many of my other characters. I do the holidays and achievements that are appropriate for them because I lack the motivation to bother otherwise. So yes, I've done What a Long, Strange Trip It's Been, it's just never going to be officially recognized. But I'm okay with that, as such motivation has made some of the more tedious holidays at least tolerable.
Roleplaying is an excellent medium in that it can be done in so many different ways. Probably the most memorable for me (and the most enriching) is when an RP storyline intermingles with in-game locations and lore. I'm never going to be able to pass by the Cenarion Refuge without thinking of the big showdown that went on there. I can't fly over the High Path in Nagrand without the recollection of burying a loved one. Shattrath holds so many memories it's almost a self-sufficient world in and of itself. And now Thunder Bluff, alongside the Lunar Festival, has nicely wrapped up a plot thread that's been in the works for months.
If you're looking for a way to enrich your roleplay and get connected to the game world, I highly recommend using the world around you. Even if you're not on a terribly active roleplaying server, grabbing a friend or two and pulling something together can be just as much fun!
Fortunately, in-game changes and events generally come with some form of warning. Static events such as the monthly(ish) holidays, patch notes, and rumblings on the Blizzard main site give you time to plan as a storyteller. The best thing to do is find something you'd like to use and decide on an appropriate motivation. Every character is going to have some sort of reaction to the impending Cataclysm, but perhaps a character exalted with the Wyrmrest Accord will have more reason to care about the attack on the Temple and the breech of the Ruby Sanctum in the next content patch. A character courting another is probably going to be easier to integrate with the Fool For Love events, and druids and shaman always have a good reason To Honor One's Elders.
Make a loose plan of action for your characters. When you hear of a new content patch with associated lore, consider who it will affect. Scour your achievement list for something interesting and set a plan into motion. Get other people in on the action to make it enjoyable and entertaining for all involved.
Roleplaying is very much a production, especially in this format. You're coordinating something that will unfold over a certain timeline and will involve other people either directly or indirectly. You have to play to the strengths of the world rather than bucking against it. Generally with these things I like to have some idea of where the climax for that particular plot thread is going to take place. In most cases, for me, it's been in a fairly public place, but it depends on the story and who all is involved. I've had things fall into place on a floating rock above Hellfire Peninsula just as easily as the center of Moonglade.
Coordinating schedules can be difficult, but if you're involving someone else in this, you need to make sure you're both on the same page. If it ends up having to be done via collaborative writing rather than in-game (due to time or level restrictions) then so be it. Far better to do that than progress with something not everyone has signed on for.
As I mentioned in an earlier post, roleplaying in a medium such as WoW is almost episodic in format. There isn't necessarily an 'end', just a series of resolutions to a series of conflicts, and in-game content provides an excellent segue between them.
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