I haven't found a definitive recommendation from Microsoft one way or the other. All I can say is that I've repeated Sysprep on a disk image myself, and I don't recall suffering any wrath as a result. The only issue I know about for sure is that after a certain number of runs, Sysprep will no longer reset the product activation grace period. I didn't find any description on Microsoft's Web site of the exact number of times you can run Sysprep before it stops resetting the grace period, though.
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