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The Boxster is probably the most fun car of the list that you made but you are looking at cars that are 15 or so years old and even regular maintenance will be more expensive on it then the others. The TT does understeer as it is front heavy (I have one) but you should only consider the 225hp Quattro version or the 2004 or newer 3.2 version, the FWD you drove is only 180hp and believe me you can feel the power of the other 2 over that one. Also with a Quattro you will get an independent rear suspension and a very different behaving car that is incredibly reliable and peppy. For me it's a toss up between the 2 of which I like better. My TT has Bilstein coilovers and all the understeer dialed out and is definitely faster than the Boxster and has a much better overall quality of interior feel but I still look forward to parking it and enjoying the Boxster. For 10k you could buy both, I paid $3500 for my TT a few years ago and have about $1500 into the Boxster all told so I managed to do it for under 5k.
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