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I did a lot of research before I got my 2000 boxster. I think you can find a nice one for $20 grand. You can definately get a nice 2.7 for that type of money and you might get lucky and steal an S. My recommendation is the PPI and an extended warranty that covers wear and tear as well as seals and gaskets. If you need a good warranty guy just send me a private message.
I encourage you to scour the dealerships that don't deal with Porsches as those dealers typically send the cars to the auction and they will gladly sell a Boxster at a wholesale price. I got mine from a Jeep dealership last year. My car had only 46000 miles on it and was in excellent condition and I got it for $19000. That same car at Carmax or Porsche would have cost me $23-$24000. I got a 3 year / 36000 mile warranty for something like $2500 or so and I have been enjoying my car and even taking her to the dealership for repairs and my deductible is only $100. They even reimburse me $30 for the rental.
I have driven the 2.5 liter cars and the 3.2 cars and the 2.7 is just fine with me but everyone has their own preferences.
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