I am a fan of 1st gen Boxsters. They tend to be very reliable if well cared for. Mine is a 98 with original motor, 106K miles, 80 track days, smooth idle, burns no oil between changes, a lot of car for the $$ I think.
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2009 Cayman 2.9L PDK (with a few tweaks)
PCA-GPX Chief Driving Instructor-Ret.