I am in the same boat with thinking the 355 as equivalent to the 993, last of the Mohicans. There are some pretty big horror stories with those cars though, including the $10k exhaust manifolds that crack. Do your due diligence with any Italian (F-cars, Lambo, Masers).
I personally view the 360 and 430 as more mechanical than art. Collectible? Maybe not imo, except for the Stradale and Scuderia.
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02 Boxster (DD sans kids)
03 Dodge Ram Quad Cab (Stuff hauler)
06 Maserati Coupe Cambiocorsa (Personal weekend car)
06 Maserati Quattroporte (Family hauler)
08 Corvette Z06 (Track car)
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