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From a fun perspective, upgrade your existing car. A 2.7 with a supercharger will be a lot more fun and cooler than a stock S.
From a money perspective the S is worth more and will hold the value better than a modified 2.7L will, also when you want to sell it will take the right buyer, tho I don't think it will be a hard sell regardless.
If you have the cash and want to spend it go for it, you only live once, just dont be diping into your retirement plan or borrowing the money for stuff like this. If it's cash then have at it.
Personally I would modify the 2.7L but that has always been my nature. Have what others don't have, which is a supercharged boxster, everybody and their dog has a S model with nothing done to it. Plus you could do what your looking at cheaper than 17k really...
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