I would scrape up some more funds and get a 2002 996. The 2002 is what the 2000 Boxster is in terms of big changes and updates. Or wait until the 2002 come down which given the credit market situation is dropping the prices of all Porsches.
New Sales are down some 20%. That's allot if you only sell 30K cars a year.
I'm looking for a C4 myself but its really going to be excessive since I only drive weekends. I have no intention of parting with me BoxsterS but I can't continue racking up winter miles on a roadster. Seems pointless. That's why I want the four wheel drive. The falling prices is convincing me its a good time to make a bad decision.
I've driven all the 996 except the GT's (althoug I rode shot gun). I find both the 996 and Boxsters to be underwhelming in the power department. The Carrera in general never had more than 300HP up until a few years ago. You Had to get the Carrera S if you wanted that. The rear engine action of the Carrera is not at all to my liking. I don't feel you should have to learn a particular type of car, before you've learn to drive period. If in the end its not a net gain in terms of speed, it seems like something you learn with no
greater benefit than just getting a mid engine sports car to begin with. Some people love making life harder for themselves then it needs to be and they chalk it up to "rewarding". But at the end of the day its personal preference deal.
In terms of which is better for you well since its a third car I'm inclined to go with the BoxsterS. I personally feel that a car at this weight should have at least 240HP, the chasis seems to "come alive" at the power point, ditto for the S2000.