i haven't had the pleasure (or horror, as some others might say) of Italian car ownership yet, but aspire to obtain something like a late 90's F355. that, and the 911 were my dream cars at an early age, and i'd love to someday go 2 for 2 on the ownership and dream realization experience.
the 911 being my dream car basically is the end of any mental/emotional debate i have about Porsche's sports cars. i HAVE to have a 911 if i am to be a Porsche owner. and i have what i consider the most true modern example short of a GT3 RS or a Singer resto-mod. but objectively speaking, the dynamics of the Cayman are better. fairly competitive to the GT3 with a lot less drama, so i have to believe that it would be better than a normal 911. the only place where the Cayman falls flat to its bigger brother is the acceleration and power delivery - although it does run just fine with my E90 M3 despite giving up almost 100 hp. that problem, of course, is fixed once Porsche releases its rumored GT4, or you take it to a couple of shops around here that will drop in the 3.8 991 Carrera S engine for you