The thing with the rolling release is, that you get a few small updates each day/week, so if something breaks, you generally know where, which makes it easier to pinpoint the problem and fix it, then after a full distro upgrade.
However, in the one year I have been using Arch as my main distro, I had only two small breakages.
The first was a recent upgrade of openvpn, which required you to move some folder from one place to the other. however this was a known breaking change, so it was announced on the Arch-announce mailing list. :)
The second happened this weekend. I had been using the infinality-font-bundle, which provides a patched fonts set that is beautifully rendered. However it seems that the developer hadn't been keeping up with the new versions of fontconfig and the had been some new options added, and after an update gdk-bixbuf2 needed one of them to function. (which resultet in missing icons) This was fixed after 5 minutes of googleing.
So not something very dramatic.
Packaging:
The package manager is pacman and the standard repos already have a lot of software. And then there is the AUR, where everybody can upload build-scripts for stuff that is not in the official repositories. Most of the time they work great, there hasn't been any software at all that I had to download from a browser.