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My thoughts:
First, look at a 2008+ - they have a lot fewer issues than the originals (coolant pipes, cardan shafts, etc.).
Second, if you are looking at a 2008+, take a look at a base. They do not have gobs of power, but I find it is more than sufficient around town, and you can always kick on the Sport mode, which makes it a zippy and fun car. Gas mileage between the two is not much different, but up-front cost is. I just bought my 2009 back in August, and for a similarly equipped S, it was $6K - $7K more expensive. Having owned and driven mine for the past few months, including in the snow (which is where they really shine), I would not go back and pay the premium for the extra HP.
Finally, look for an optioned-up one - mine has almost everything but air suspension, and I love the heated seats, heated steering wheel, PCM (I hardly use it for nav, but the iPod navigation and Bluetooth cell phone connectivity have made it well worth it), and interior lighting options.
Just my $.02.
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Steve Wilwerding
1998 3.4L Zenith Blue Boxster
2009 Meteor Gray Cayenne
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