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I have a 986 base. I sometimes wish I had more power - but not enough to want to sell mine, buy another one, etc.
only think I don't like is the plastic window. definitely go 2003+.
I'd look at dealers and see how cheap/old you can go and still find a good CPO car.
once you do your hoemwork, you'll find where the "sweet spot" is for how new y ou can go and whether it's a base or s. obvioulsy, in general, more miles = cheaper. older model year = cheaper. base is cheaper than an S. older S might cost similar to a newer base. try them both and see how badly you like hte power of an S. newer base might be close enough to the older S to make it a better buy.
try to get litronics. try to get the sport suspension if you can. get 18" wheels instead of 17"s. full leather is a nice option if you want the interior to look more upscale. the 987 interior looks better than the 986.
whatever you get, yhou will love it. the car is so much fun.
in your price range, I think I'd go for a newer/lower mileage BASE 987.
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