[renzop]

Really its up to you. And you shouldn't let other people's opinions influence you. Also you asked on a Boxster board so of course, there is a Boxster bias.

If I had 60 large to throw around here are some of the factors I would use to make my decision:

1) Am I a convertible guy? Is open air motoring really important to me
2) How risk averse am I? The 911 is a used car and there is more potential for it to have expensive problems than a new car. If the 911 is a Certified Porsche car then the risk goes down considerably.
3) Which car do I like the looks of more? I would ask someone else to surprise me with this question and whatever first popped into my head would be the right answer.
4) Is the miniscule back seat of the Carrera of any benefit to me?
5) Do I really enjoy fast acceleration or is reasonable power and good handling more important?
6) How long do I plan to keep the car? If a short time (like 1-2 years) then I am going to take a big deprecation hit on a new Boxster and much less on the 911. Even buying new vs new the Boxster depreciates faster.
7) How important is it to get all of the options exactly the way I like them? If you buy used you get what someone else wanted. If you buy new you have the option of ordering a car exactly the way you want it.

I would ignore the comments that implied that the 997 is hard to tame or needed AWD to be safe. If you were looking at a '60s '70s or '80s 911 it would be another story but the 997 has had all of its vices tamed through suspension evolution and electronic gimcrackery. Both the Boxster and the Carrera are great handling cars and as long as you use a little common sense and don't exceed your abilities then they will be very stabile and planted.

Whatever you decide to do, once you make the decision don't look back and there will be no regrets. I am sure you'll be happy!

Regards,
Alan