My general procedure is as follows:
1) Check the SBS team blog. When updates have issues, they will usually get a blog post up.
2) Critical updates get applied same week, but I wait until the weekend unles the security advisory has something "in the wild"
3) Important updates I wait two weeks.
4) I back up right before starting and I back up right after finishing and I DON'T replace the first backup (need the option to roll back.)
Simple as that.