I just wanted to mention that all Caymans, from 2006-present, have the exact same transmission gear ratios and final drive. It's annoying as hell because 1st and 2nd gears are way too tall, and 5th and 6th gears are too short. As Car and Driver recently stated, it's like having a transmission full of 3rd and 4th gears. And you better believe Porsche did this intentionally to keep it less competitive with the 911. (BTW I'm talking about the manual transmission, not PDK. Also I'm referring to the 6sp manual. Earlier Caymans came standard with a 5sp)
As far as Cayman resale values (looking down the road), resale value for the S models will be higher. Most people (for better or worse) prefer the S model, or GTS, etc). The base models are less desirable.
OP, what model year S2000 did you own? Because I owned an AP2 for 4 years (was my first RWD car) and I didn't think the handling on track or off was remotely "tricky" as you described it.
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Current: 2023 GRC Circuit Edition, 2012 C63 AMG P31
Past: (2) 2000 MR2 Spyder, 2017 GTI Sport, 2006 Porsche Cayman S, Supercharged 2013 BRZ-L, 2007 Honda S2000, 1992 Integra GS-R
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