Indeed, comes down to what you want out of your system. Also update frequency isn't as important as the software you choose to run. I happen to mostly use stable stuff that doesn't change much: openbox+xfce for wm, mplayer, and palemoon specifically because I got tired of firefox adding shit I didn't want and taking away stuff I did. I use gentoo and generally do an update every few weeks, but it's been awhile since I did an update and anything radically changed.
With my servers it's much the same story. Most of the stuff I'm using (apache, postgres, nfs, etc..) has been stable for some time, so though I do an update every few weeks, very little changes.
On the other hand, if I was using the latest ubuntu and kde/gnome and vlc and firefox and all that, every update would probably entirely change my system. One day I'd launch firefox and find out that the URL bar was now on the bottom or something to make way for a big facebook widget and my program menu would disappear because gnome decided that Microsoft was on to something when they eliminated the start menu and providing too many options in a list like that was confusing to users.