I have been on this forum for almost 4 years of which 3.5 years was with ownership of a 2000 Boxster. Loved the car. Sold it and bought a 1999 Carrera. Had it now for 3 months. Very different car and driving experience. Why buy a 99 Carerra? Horse power! Love the performance. My 99 Carerra will leave a 2004S wondering what happened. Porsche has always put the 911 ahead of everything in regard to performance. Now, my 99 would not be able to walk away from a 2013 BoxsterS, but it is a few years older. The Boxster is a better handeling car but the Carerra feels bigger and is a better long distance cruiser. Both are wonderful cars.
P.S. I bought my 99 for $20,000 and immediately put $2,500 in it with an IMS, rms and new rear tires. Beautiful car with only 27,000.