I don't see why you would have any problems if you having everything done at the dealer. Any car that is maintained properly will run well for a long time. And if your getting concerned about the $2k a year, you can probably do most of the things yourself. These cars are easy to work on, and even if you don't want to get too technical, things like the replacing the cabin filter are easy enough. Also, a jiffy lube oil change is no different that a dealer oil change except for the price.
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1999 Ocean Blue Metallic Boxster - blueboxster.com
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