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My $.02, when I bought my MY01 base in 06, I didn't care if it was the base or the "S". The move into a Boxster was such a quantum jump up from what I had. It might be the same for you with respect to 03S vs 05 base.
With the 03 you are getting a MY that has had most of the kinks worked out of it (set aside $ for the IMS refit). And it has the glass rear window, which to me fixes the biggest non-mechanical downer of the 1st gen cars. I hate doing the chop.
I think you'll be happy as long as the 03 is in good shape (get a PPI in any case).
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2001 Boxster, 5 spd, Seal Grey
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