5 minutes is a long time for upgrading WP, as far as I’m concerned. I think it might have taken 5 minutes total to upgrade all three of my current WP installs and check/fix plugin issues. Mind you, I use the subversion method of upgrading. If you have shell access and can run subversion, it is so incredibly easy to upgrade WP with it that I don’t ever want to go back to the download-unzip-upload stuff I used to do. In a post I referenced earlier, Matt said:
Upgrade your blog to the latest WP. This shouldn’t be hard. There are plugins for it, if you’re techy use Subversion, there is the standard FTP method, and finally Media Temple, Dreamhost, and Bluehost (through SimpleScripts) all have been pretty good about having their one-click upgrade systems ready with new versions within a day or two of a release.
I’m techy, sure, but I don’t know much about subversion other than it seems to have replaced CVS and I didn’t know much of anything about CVS other than that people working on big OSS projects seemed to use it. (Okay, I know a little more about what subversion and CVS are supposed to do, but I’ve never actually used a check-in/check-out/versioning system.) I literally just installed subversion with the package manager on my system, then used the commands given in the WP Codex. Not very techy-like. Done.