Re: New '07 987S vs 2004 911 Anniversary Edition (345hp)- HELP!
Don't forget the following salient points
When Porsche produced the 986 Boxster and 996 they had very limited funds to produce the car they would have liked to. Whilst both these cars undoubtedly "saved" Porsche as an independent sports car manufacturer because they were such good products, it is no secret that with the 987 / 997 they had the funds to properly develop the cars. Look no further than the interior to see that.
The 987 /997 is a seven year newer design, and you can't turn the clock back. I believe you would notice that going from a 987 to a 996.
You would suffer a lot less depreciation if you bought a used 996 than a new Boxster, but that is the case with any used car / new car purchase. The 996 would however cost a lot more to run and maintain than a new Boxster.(older, more frequent and expensive service requirements).
Drive the cars, see which you prefer. If you prefer the drive of a rear engined Porsche, and a lot of people do, not forgetting that a 996 would probably be quicker than a 3.4 Boxster in a straight line, if not in the twisty bits.
Do you want an open top or do you prefer a coupe?
I would worry about buying a second hand sports car whose owner(s) I didn't know. How was it treated by the previous owner(s)? Was it looked after carefully, always warmed up before hoofing it, or has it been thrashed to within one inch of its life round a track?
With a new car you can specify it exactly as you want, in your favourite colour, with the wheels and other options you prefer.
All these things need to be taken into consideration.
Me? I've just sold an 05 Boxster S and have a new 07 Boxster S 3.4 on order for October delivery. I wouldn't consider a 996. But that's my personal choice.