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1. I don't know about the base Boxster, but the S performs beautifully when pushed hard.
2. Yes a newer year is always better. But by the same argument, the 04 is better than the 03, the 05 is better than the 04, etc., ad infinitim. What you need to look at is the condition the car is in. A great quality 02 with 33k miles is better than a great quality 03 with 50k miles.
3. The Boxster security system is two-fold: First is the traditional alarm-system that monitors the doors, trunks, oddments tray, windows, and top. It also has infra-red motion sensors that monitor the cabin. Second, it has an immobilizer system that disables the engine unless the key with the properly coded microchip is used to start the car. In addition, the keyless entry system uses a rolling-code transponder which makes it difficult to snatch the code from the signal and unlock the doors. From what I've seen of factory alarms, it is quite good.
4. Nope, and alot.
5. Insure it like any other nice car. And get an extended warranty before the factory one expires. Make sure it is an "exclusionary warranty" meaning it covers everthing on the car, except "consumibles" like brake pads and tires. WarrantyDirect.com's SecureCar+ w/ Emissions is such a warranty.
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