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I wholeheartedly second the opinion that the "S" model is what you want. The regular Boxster is a great car, but if you like to set the backroads on fire, the "S" has what you need.
If you're shopping in the $30's, you should be able to get an M97 powered 2008 if you shop carefully - more torque from the extra displacement and no IMS issues. Be sure to verify I found an $40K '08 CPO for my Dad last winter and it is a screamer with a much better road feel and interior to boot -- worth the premium if you've got it.
For me, the $/fun ratio of a 00-04 S can't be beat, but I wouldn't go over $20K on any 986 (my hi mile, swapped motor 2000 S was 10, with no disasters yet).
If you're going to buy an M96 car, may as well stick to the 986 and save your money - my $0.02.
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"Betty" -- 2000 Boxster S, Triple Black, loaded except PSM (sold to a good home)
"Veronica" -- 2008 Boxster S, Arctic Silver on Blue
"Maleficent" -- 2007 Cayman S, Red and Black, TPC Turbo 3.6L 460 RWHP, H&R RSS Coilover / TPC stage 2 suspension
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