I looked for a Boxster for a loooong time in the $25,000 range, thinking the same as you do, older faster S or newer more refined and slower base, until I got this:-

'04 S, 40,000 mls, 1 owner (no lease), triple black, Porsche certified with full Porsche warranty until 2014 or 100,000 mls, totally flawless, all service records, first owner is anal about his Porsche, he traded for a '10 S, $ 23,000 with 1.9% Porsche financing..... hard to beat IMHO. Heck, they put new HTZ 3 tires, brakes etc on before I got it.

Point is there are so many Boxsters out there for much less $ than mine but this one is just like a new car, never has seen rain or snow. I just waited for the "right" and "clean" ride!

Good luck!

has anyone up here gone from the 986 S to a 07 08 3.4 S and if so what are your impressions ?

Yes, I went from an 01S to my 08S LE. The extra 50hp is sweet. Like the 987 interior better, like the 986 exterior better but I don't see the exterior when I'm driving. The shifter is way better in the 987 too (although you can fix the 986 with the 987 shifter).

My 08S has been one of the best new cars I've ever owned for reliability. Have 23K mi on her, so she's no garage queen.

Bottom line, I've never missed my 986.