Being a core PC gamer very early on in my childhood (being that the family wasn't interested in getting consoles at all) I haven't really burdened myself with a nostalgia considering either the Xbox or Playstation controller (or Nintendo's, for that matter). Only being able to play with them when over at friends' places in the past meant that I put in roughly equal hours of both.
I think they both have their pros and cons. The symmetry of the Dualshock has a graceful simplicity to it that makes it a breeze to readily learn. My elder brother (who is a complete imbecile when it comes to console gaming) picked up on the Dualshock control scheme somewhat faster than he did when he started playing Halo on the original Xbox (the revised controller, not the hilarious awesome and cramp-intensive original chunk of plastic lol). It also helps that structurally the Dualshock hasn't been altered too much since it's PlayStation iterations (besides perhaps fractional differences in width, I think). People coming in from earlier generations won't have many problems adapting to newer control schemes. XboxOne seems to be going for the same approach: why fix what isn't broke, right?
But again, it also depends on the genre and the way the controller is used and mapped in games. From personal experience menu-intensive games like RPGs are much less finicky browsed by a D-Pad and bumper buttons, whereas in shooters clearly triggers and C-sticks reign. There's two extremes there, and it's not always as simple as that, of course. The majority of fighting game players swear by the stick, but a D-pad can be a very easily acquired taste.
Katamari is a very interesting example. I tried emulating a Katamari game and with my 360 pad it was basically nope.avi, so there's that. Again, all comes down to how the buttons are mapped by a game and the way they use it. MGS Peace Walker in the HD edition greatly benefited from having sticks in a 360 controller that didn't require a whole lot of reach.
Personally while I enjoy the Dualshock's design, I absolutely fucking adore the 360 controller's curved aesthetic for looks, if nothing else. The triggers and shoulder buttons are far superior for shooter games with solid, tangible pull to them. The d-pad was indescribably garbage, but it looks like that would be sorted out in this new iteration.
All in all, though, I think the "40 changes" made to the controller will likely be mostly internal and not outwardly noticeable at first. Mayhaps they've made wireless controllers more responsive by a couple of statistically significant nanoseconds, I don't know.