Besides the plugins that have its own managers (like NI Komplete, Play, Cakwalk etc) I never really update unless something is buggy or broken. Once - or maybe twice - a year I sit down and do a update session of my plugs and leave it at that. I usually do this when doing major updates to the OS. If the plugs works, I don't see the point in stressing about updating plugs, even if the update contain some fancy functions.
For the past few years I have made a point in not caring about "system administration" and rather use my stuff to make money and have the time to get drunk instead.