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If you haven't already done so, go drive them both. It may help you decide what's important with regard to the driving experience.
I've owned a base and an S..at the same time. Both are great cars and very enjoyable. I also have an old AlfaSpider that is thrown in the mix!
It was weird. I could the Alfa for a few days or a week and truly enjoy it. I'd never drive it and think that i'd rather be in one of the Boxsters. Likewise, driving the base car was a blast.
I will say though, that every time I'd get back in the S, I'd have one though...this is the best car out of the three...by far.
From a maintenance standpoint, you mentioned that the 99 had all its maintenance done, but not the 30K mile service. Is there records to support any maintenance? Basically, up to 30K miles, the only scheduled maintenance is oil changes. That's not a lot to go by.
There are other concerns with cars this old. What shape are the headlight assemblies in? even used ones are expensive. What about the top and the rear window? How's the leather on the seats? Does the car have both keys? There are lots of $$ items on these cars that have nothing to do with maintenance but might help you with your negotiations.
Either way, one thing is for sure, you're gonna love it!
Bottom line, spend some time with both and see if one draws your interest more than the other. It might make the decision easier.
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