Keeping WordPress up to date

Updating WordPress is kind of pain. I can completely understand why many people do never update their (non-personal) sites. This is not a large WordPress installation. One site, roughly half a dozen plugins, one theme, and that is it. Nevertheless, today I made the effort to back up the data base and files and to update everything. Two plugins failed to work properly afterwards and it took me two hours to fix everything. However, don’t get me wrong. The heaviest problems I got did not originate from one of the plugins itself, but from the way I used it. Meaning, it was my own fault. Still, a pain.