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He can, but if he's done most of the other quests, then he won't be able to finish in the normal game.
I can't find it right now (not at my computer), but there should be a timed global variable (probably something involving "keep", "stronghold", etc, and has a high number). If you change this to 1 (and maybe change areas), you'll get the next stronghold quest.
Incidentally, I agree with you entirely. The game assumes 7 days between each stronghold quest, but the way I play, 3-4 days would be far more appropriate. I don't have the scripting ability, but it wouldn't be too hard for someone good at scripting to work out.
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