I don’t think it’s just personal experience. I had a similar feeling as the OP, but my feeling happened at a very specific time. I upgraded my MacBook from Snow Leopard to either Lion or Mountain Lion (I cant remember which version it was), and overnight I went from having my entire life spelled out on my calendar to basically not being able to use iCal (it might have been renamed by that point as well) at all.

The new version of iCal’s only purpose was to look pretty and offer very basic functionality. The older version might have started looking dated, but I could use keyboard shortcuts and see details about my appointments easily at a glance. The new version didn’t even want me to know details existed.

The same story played out in Mail.app, Address book, iWork, etc.

MS’s new “Modern” apps show that the same influences have driven Windows development in recent times as well.