The cost delta was just a few grand when I started looking 3-4 years ago. I looked at both boxster and 996 cabriolet models, and let a beautiful C4S slide by me without buying at just a little more than what I ultimately paid for my 986s. At some point, I realized that I didn't bite on the C4S because what I really wanted was the boxster..

The fact that this left a little cash in the toy budget for extras was nice, too.
I too am under the impression that prices for the BoxsterS may have rebounded just a bit, with 996 prices slowly hovering lower.
But dang, I just yesterday saw an 01 BoxS with mileage in the 90K range, equipped with PSC and PSE, plus an Aero1 kit (long tail/dynamic spoiler delete), sell for just under $9 thousand on ebay. So deals are still out there on the 986s. And for now at least, I would still choose the boxsterS over the 996.
Now a first generation well-kept CaymanS.... I might have to expand the stable if the right car for sale tried to run me over. Would probably have to trade in the boxster on a Miata if I also aquired a Cayman, because 2 Porsches in the motor pool just seems decadent (no offense to you heathens that can do this without guilt) and I'm not ready to give up roofless riding.
And you all leave Jake alone, he seems to be more mature than half the posters on this forum, and while I'm not partial to his fluff threads - the point of a forum is to promote dialogue, and his posts seem to achieve that goal, and without being offensive except to those seeking to take offense.
Furthermore, at the rate his grammar and spelling are improving since his first unintelligible posts, he will soon be teaching college English classes!