Yes, there have been breakages, but none very bad and thus not very memorable. Interestingly, some breakages were due to windows update doing something bad since I was dual booting.
Before switching to arch, I used ubuntu for years, and that was not nearly as pleasant an experience. Upgrading ubuntu versions always failed in some horrible way for me and I had to just reinstall the new version instead, and the way ubuntu is put together made it a horrible experience if you ever needed to install software that didn't jive with it(like something that required an updated version of some gnome dependency).