I have a "Non-S" 2004 Boxster. I don't regret it at all. I drove a new S the other day and I didn't get a "holy $hit I wish I had this" feeling, but I am sure the stopwatch would tell the difference.
If you plan to have other cars-porsches in your life then everything will be a step up.
I would say the Box is more fun and can be driven faster than many cars with the same HP or 0-60 numbers.
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2004 Boxster - Carmon Red/ Black-SOLD
18" Carrera Lt, Painted to match roll bars, PnP Rear Speakers, Sports Tailpipe
2004 Tonka Truck H2
05 S - looking...
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