IMO Cayman S is a way better car than the 996 C2 in pretty much every respect. Better handling, comparable power and power-weight ratio, did I mention better handling, way better interior, more modern options, and probably in better shape, with warranty, for less money.

But that being said, if you regret owning a Tip all the time, you are a fool to buy another Tip car. Just buy a manual if you want a manual.

Personally I would wait for DSG even if I had to wait a year.