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Don't get used. First, the cars you're looking at are going to have been driven hard. For the money you're spending, its not worth the risk. Imagine your fun when you realize the car you bought is a three year old POS. When you get the repair bills, you'll really have some fun.
You're spending alot of money. Spend the extra 10k (or get a cheaper car) and get piece of mind. Especially the piece of mind that comes with a 48,000 mi service warrantee.
Second, on top of being driven hard, you're looking at convertibles. Regular cars get noisier and noiser with age as all the nuts and bolts get looser and looser. Its 10 times worse in a convertible. They're allready 10 times noiser than the equivalent hardtop.
If you're looking at the TT 1.8 or the Saab, the 1.8 is underpowered. Plus, Saab's are cheap. I got one a year ago and they're even cheaper now. Just beware there's a planned model change as soon as next year.
And with a convertible, in my opinion, a glass rear window is a requirement. No matter how expensive your car is, if your rear window is yellow and cracking, your driving a POS.
In my opinion, in the 40k range, you're looking at:
TT
Saabs
Volvo (I don't like them, but this is a list)
BMW 325
SLK
Get insurance quotes first too. My insurance charges me 1000 for my saab, but the 325 would have been almost 2200.
And test drive everything. Its a lot of fun.
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