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If it were me, I'd go for the newest (Option 2). You get the updates that happened in 2002 and the replaced water pump (although you didn't say how many miles are on it... a lot of people replace every 40k), AOS and IMS/RMS. My understanding is there isn't really a good way to "look at the IMS when the clutch is off and determine it's fine". I _think_ you need to pull the bearing to be sure, and at that point replace since you can't reuse once pulled. Of course for the $5k price difference you could have the pump and IMS done on the 1999, but I think the updates the 2003 has are worth it. It's too bad you don't have service records all the way to the beginning, but the last 30k miles worth is useful at least.
Good luck with your purchase!
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2002 Boxster S
2004 911 C4S
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