Rp challenge-sign ups
Adinas and I, on our first characters, employed the "World Tour Method" of questing. Basically, this method is that you work your way rigidly up the "brackets" of zones by level before moving to the next "set". For example, in your case, you'd quest in Eversong Woods, Durotar, Mulgore, and Tirisfal Glades (in any order you like); once you did all of those, you'd move up to the next "set" (Ghostlands, Silverpine, and whatever the next Horde zone is for orcs and tauren).
While the purpose of this method is actually to maximize your reputation gain and quest achievement progress, it serves the secondary function of just about guaranteeing that you will encounter precisely nothing that can kill you (unless you run flagged and get ganked). Since you mentioned that you're not worried about how long this challenge will take you, I thought it might suit your intentions nicely.
Also, may I also suggest that your rules make an exception for a single, macro'ed whisper that you could send someone (like, say, "I'm sorry; I'm doing the Ironman Challenge and must be IC at all times. But you can reach me as [main] with any questions") so that they don't assume that the person resisting OOC is doing so for less than honorable reasons?
And one last: Why not do your character journal on CenarionCircle.org? It'd be fascinating to see how the rigidly in-game world winds up translating for your characters and anyone else's who does this.
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