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This is a shot in the dark... If WotLK is anything like BC, and as long as a character hits 70 before WotLK is released, that character won't have to set foot in a single current end-game instance (or ANY current instance for that matter). Just by leveling from 70 to 80, they will be up to date in gear that mostly supercedes current gear.
If that's the case, I guess the latest time to reroll would be a few weeks before WotLK releases. Or however long it takes you to hit 70. *shrug*
If WotLK is nothing like BC... then I dunno.
I'm not entirely sure how they could avoid it though. In a game like this where soloing is a perfectly viable (and often preferred) way to level, they pretty much have to give quest rewards/drops that are appropriate for a player's level. A quest I can solo at 80 should give a better reward than any gear I had at 70, regardless of how tough it was to acquire. Kinda sucks, but as I said I think it's unavoidable.
In a game like EverQuest on the other hand, soloing was out of the question except for a few select classes. Even then, quests (despite the name lolz) didn't really exist like they do in WoW so the few classes that could solo weren't actually getting gear along the way. Gear almost exclusively came from groups and raids in EQ, so when an expansion came out that raised the level cap, hitting that cap didn't guarantee you were up to date on gear. Some of that gear you had from the last expansion may still be useful. There was a stricter progression in that game, and if you got behind, it was considerably tougher to catch up.
Oops I rambled way too much. Bottom line: Unless Blizzard is drastically changing the formula of the game, then the latest you (yourself, your friends, or your entire guild) can reroll and not be left behind will be a few weeks before WotLK comes out.
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