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It seems that you are leaning towards the SLK. Especially with your statement that you barely fit into the Boxster. So it seems that if you bought the Boxster, you would be uncomfortable driving it and miss the options on the SLK.
Maybe neither car is right for you. On the one hand you have an 'uncared' for 2 year old SLK with options, and on the other hand, a well-cared for (babied) 5 year old boxster that is too small. Hmmmmmmmm.
Since I fit in both cars, my choice would be the Boxster. I usually buy my cars new, but if I had to buy a used car, it would be the one that is 'well cared' for. You don't want to buy someone else's problems on 'uncared for' expensive cars.
Whatever your choice, good luck to you.
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