I did another upgrade of WordPress without a hitch the other night. I was talking on the phone with my aunt at the time. I often hear tales of woe when people talk about doing the upgrades. I think the issues that they run into must have something to do with the plugins. Some sites, like a certain one that will go unmentioned in this particular post, have loads and loads of plugins, so a core upgrade can turn into a true nightmare of dependencies. There was one major update (maybe a year ago now) where WP added features that used to be handled by the most popular plugins. How often do you review the plugins you have installed? Are any past their prime? I currently have three that I don’t really use at all anymore, and maybe 6 or 7 beyond that.