I have not noticed any difference in braking between the Boxster and the 996. My guess is that the pads might not be OEM so the initial bite may seem lacking (or maybe whoever did the recent brake job didn't get something quite right).
And yes, the 996 feels quite a bit bigger and heavier than the Boxster, but it really has a lot more go-go-go when you step on the happy pedal. To me, the Boxster has a classic sport car feel whereas the 996 is really a GT.
Owning both really is the best of both worlds.
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1999 996 C2 - sold - bought back - sold for more
1997 Spec Boxster BSR #254
1979 911 SC
POC Licensed DE/TT Instructor
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