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if the boxster / cayman will be a daily drive r- get the newest one you can, get it under warranty / CPO / etc.
if you have DD transportation covered and the boxster is a pure toy, and you are on a budget, an older one is not a bad idea.. if you can live with the prospect that it *could* break and *could* be very expensive,a nd you would not be able to drive it for a long time until you had the funds to repair it - then maybe an older one is worth the risk.
i agree with what another poster said - an older used boxster will be JUST as much fun as a newer one. newer is better, and if you test drive an 09, and then test drive a 99 - yeah, you'll want the 09...but if you went and test drove a 200hp 98-99 model...chances are it will plastera smile all over your face just as much as the newer one will.
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Cars:
2007 MDX - Wife's mommy mobile
2006 RL - My daily driver
2000 Boxster - Ocean Blue Base 5spd on Black Full leather. 18" wheels and M030.
Boxster mods I've added: Rear speaker kit, Painted Calipers, Painted Bumperettes, Painted Center Console, 987 Shifter Assembly, 3 Spoke Steering Wheel, Clear side markers, 03+ rear lights, de-snorkeled.
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