Having recently acquired my own Boxster (2002 S), and having it be my one and only car, I too am a bit concerned about the maintenance costs of owning a car like this. But you really have to determine your own threshold of pain with cost. The cold hard truth is that if something breaks, it will most likely be expensive to fix. But from what I hear from people, Boxsters are reliable cars (espeically later models that have many of the bugs worked out) if they are maintained properly.
For peace of mind I will be getting an extended warranty soon (I still have a few months of the factory warranty left). Many people here are very pleased with WarrantyDirect. For about $3000 (less if you don't mind a deductible) you can get a full bumper-to-bumper warranty for 4 years and 75k miles (and I mean full: they cover anything on your car except "consumibles" such as brake pads). There's also a wealth of information on these forums and on the web about how to care for and service your car yourself.
You also have to evaulate your own driving habits. Are you a high-milage driver? Are they city miles with lots of stop and go, or do you tend to put easy cruising miles on your cars? Are you a track-whore (fess up now!
) ? Do you love to rev the engine and drop the clutch at every stoplight or light up your tires whenever you get the chance? Do you absolutely require the best tires with the most grip or can you deal with slightly lower performance for tires that might actually last you more than 5k miles? (Hey I know an autocross nut that buys 5-6 sets of tires a YEAR)
If you're like me, who drives about 5-6 miles to work every day and a bit on the weekends, doesn't push my car hard, drives 10k miles or less in a year, and never races it, then you will probably be fine if you get a good vehicle. If you're an agressive driver with a lead foot and a love for mashing the brakes then you'll most likely have a higher risk of needing extra maintenance costs.
Porsche tends to make vehicles to be driven and require little maintenance. What other cars only need the oil changed every 15k miles or 2 years? Even my 01 Honda Prelude (which used full synthetic oil) needed an oil change at least every 7500 miles or 6 months.
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