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i have a 2001 Base. Really like it.
But if I were in your position (i assume you dont have kids or dont plan to have kids in the near future), I would get the 09 S. The boxster is a great car, easy to drive fast, looks cool and happy to be driven daily. I use it as my DD.
Having had the 2001 base for a while now, ive found that small bits and pieces are starting to break due to wear and tear. I've done the IMS, RMS, I did the suspension overhaul, AOS, stereo etc. I dont mind the maintenance.. .as i expect it for a 13 year old car. Dont get me wrong, i love my car. the engine is strong ... the suspension is great (now) .....but i can start to feel the bits an pieces of the car getting tired.
I know you are not considering the 986 ... but my learning here is .. in the future, i'll get a much newer one, so less wear and tear. So i encourage you to get the newest one you can afford. If no kids on the horizon ... just use it exclusively as your DD and sell the A3.
Also, the 09 ... ive seen some really cool looking ones with minor exterior mods. u'll be happy driving it for the next 10 years.
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