What's worked for me has been to read the archlinux.org homepage before I upgrade (maybe once every few days). If there are any breaking changes they are listed along with the recommended method for handling them. If I somehow fat finger a command and it doesn't go smoothly then all I have to do is jump in #archlinux and my issue is resolved in under an hour.

YMMV of course but I've found the entire Arch experience to be pleasant and it fits my work flow, but I understand that it doesn't fit everyone's.