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Originally Posted by mikes_box
Price not being a factor, just looks and style which would you buy..
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I used to be a VW guy, so this isn't completely biased. In short, it's an image car. That's it. It isn't especially fun to drive, the 1.8t is one of the more boring engines on the market, and when it comes down to it, the TT is a tarted up fourth generation Golf. That isn't to say it can't be an enjoyable car to own, just that it isn't a performance car on the same level as a Boxster. The chassis is floppy and the engine is pretty laggy, especially in 225 form.
On the flip side, the TT has a more modern and higher-quality interior than a 986 Boxster. It is going to be more comfortable and probably get better mileage. Quattro is a cool technology, but in that generation TT, all it did (aside from let you go in the snow) was provide loads of boring understeer.
Reliability-wise, the 1.8t has know to need a few things from time to time (coil packs, there has been the occasional sludge problem if the incorrect oil is used), and it is a VW product... so, over time, it will most likely nickel and dime you.
Now, if you're stuck on the TT looks, go for a 3.2 VR6 car. Great engine, and it sounds incredible. Here's a Top Gear review, complete with Clarkson's um, unique style:
http://www.youtube.com/watch?v=rnXoLJclfng