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Of course it is your decision but you are asking for our perspective. For me there would be two factors in this equation. The money and the fun factor.
I originally went with a 2001 Boxster base and never even tried an S. I stayed away from test driving anything new or anything at a dealership. The reason? Once I tried something new or something superior such as an S model I likely would have been smitten. Once I feel the need then I might head into something like that.
The $$$$? Would new be worth it? If you want to put out that kind of money then fine. For me I want value and would be looking at a Cayman(2009 or newer = ims free). Would new be any more fun than old? You have tried it - you know. I have 42k miles on my 2001. It has some rattles and I know I will be facing replacing parts in the next few years likely. If $$$ was no object I would go for new definitely. But don't forget in a few years that new car will be used and Porsche will be tweaking the Boxster to make it a bit superior to the previous year. Good luck with your choice and let us know what you do!
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