Given this is a Boxster forum.... I'm probably a minority in prefering a barebone Carrera (997 only, don't like 996 at all) over a Boxster. Cayman is certainly a great option.
I usually don't buy cars that are fully loaded because they are always overpriced. For example, you can get better sound upgrade aftermarket (at same or lower $)than getting Bose upgrade from Porsche. Besides, this is a sports car, I don't care about the sound system that much (engine/exhaust sound more important). Nor do I care about leather dash or other comfy/lux options. PASM, yes, Sports Chrono, yes, performance-related upgrades, yes yes yes....
So, IF I can afford a barebone Carrera plus some performance-related upgrades, then I'll take it over a fully loaded Boxster S. But to save a few $ for a Cayman... gotta think it over.... definitely have to drive it first....
Don't forget great options like an used 993 Turbo or 993 4S, great looking cars