[Perfectlap]

Well I'm not sure if you drove a 997.2 but I had the opposite experience driving 997.1S and 996S back to back. The newer Carrera felt even more insulated, way too much like a road car. Not at all like a 964/911 of course. It seems the more powerful those cars get, the bigger they get, the less feedback, basically kinda of too engineered (some call this boring but you can never get too bored in any Porsche). I've heard 997.2 GT3 owners complain of the same after ditching the 996.2 GT3.
Since the Boxster has been very consistent and true to its original proportions from 986 to 981, and has NOT undergone the bloat of the Carrera during those same years, it's easier to compare the changes to a 1997 Boxster, from a 2000 from 2005 from a 2009. Personally, I don't really notice a big difference as far as the S models until you get to the 2009 DFI engine.
I find the 1997-99 Boxsters to be the most "crispy", although the one I drove had some weight savings worked into it, it felt like a inherently light car and the five speed seems to work better with that 2.5 engine than later Boxsters. More of a "using all the power all the time" proposition which is really what you want in a roadster. I think a manual transmission Boxster Spyder is the best Porsche driving experience for under $100K going -- lower COG, RWD, Mid-engine bliss. The Cayman S I drove was nice but less weight on top is always better imho, the 987 doens't need the extra rigidity at the expense of higher COG. The Carreras are just too big now to have that short-wheel base sports coupe experience anymore.