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Traded my 2015 Base with 34k miles 19” tires ( Michelin’s ) for a 2013 S Crono with 28k miles on it . Ride seems choppy compared to 2015 . I think it’s the Pirellis 20” seem to be harder tire.
I LOVE silver on the 981 Boxster and wish I could have found one. Such a limited market right now, especially up north.
Keep in mind, you have more rubber to play with on those 19's so that will contribute to the ride difference. I recently switched from P-Zeros to Michelin PS4S and agree that the Michelin's are much more compliant, and I was comparing equal sizes. So in your case going from 19 to 20, Michelin to Pirelli, your observations make total sense to me.