You can't really compare unless you are referring to a specific series of 911. I have owned two 911's and have found there to be big variations between the different series (964, 993, 996). I will say that I do enjoy my S2000 more than my Porsches (can't believe I'd ever say that). It's just more fun to drive. I feel like I can drive it as hard as I want without worry. With my 911's, I was always paranoid that I would break something very expensive. Which, invariably will happen so you better have a few k sitting around for those occasions.

From a pure financial position however, if you can afford the maintenance, there is NO better car for holding resale value than a used 911.

Don't see myself going back to the 911 anytime soon. I'm not wild about the 996 styling and the interior trim (which is almost exactly the same as the boxter) is just atrotious, shiny plasticky crap everywhere. The 993 was just a much nicer looking car IMO.

 

I'm on the fence (but leaning more towards s2k) between the 993 and s2k. I have taken extensive test drives of both and here are my impressions. 993 plenty of power over 4k unbelivably stable even on very poor road surfaces. Braking is top notch as is handling. I tried to induce oversteer and car held firmly and car also fit me very well 6.2 250+. S2k Handles great, brakes great, power over 6k. I found myself driving at high speeds more in the s2k because you keep wanting to redline it. The fit was a little tight but not too bad. So I enjoyed the performance of both but the advantage of the s2k for me is it is a convertible it will be my first new car it is cheaper and it will have a 3 year warranty, so that is why I am leaning more towards s2k. Hawkeye I hope my ramblings have helped a little but the best advice is to test drive both. Remember most of us car nuts agonize because there are so many great cars we want!

 

Thanks to all. I really appreciate everyone's input. I think I'm going to plan to win the next lotto so that I can have them both and put this issue to rest.
I think I'll just put a little money into smaller upgrades like hardtop and better stereo and play it by ear. It's not like I'm driving a beater...
Porsche may be in the future, but the S2K is mine now, so I think I have my answer.

 

Tomorrow Superlotto (CA) jackpot is $115 mil.