Beautifully said DFarron!
I played Pebble and Pasatiempo on back to back days earlier this year and have been lucky to play Cypress twice. My second loop around CPC really helped illuminate the subtle things whereas the first play my jaw was on the floor at every moment (but that's another thread.)
Doing my best to separate out the experience, resort v private, and history aspects there are two things that Pebble has over CPC: a longer sustained high of All World holes (6-10) and a better finish with 17-18.
Cypress has better presentation, storytelling/routing, greens (size, shape, contour, diversity), opening holes (who cares about the hedge or the range 1 is an epic hole with a great green), and inland holes. Simply put, it's more complete. In music terms it's a no skips concept album with big radio singles and that funky hidden track at the end
. Pebble might have more radio singles, but you're likely to hit skip a few times. One is Abbey Road the other The White Album, one is Kid A the other The Bends.
We're splitting hairs here between two iconic courses, but if forced to pick one over the other, it's Cypress and especially so once you include all the other extras. Given a 10 round split with no 5+ hour rounds, I'm taking Cypress 6-4 and that's because of how much I loved the Pebble highs.