I have to update our WordPress installs. I’m not looking forward to it.
Upgrading wordpress itself isn’t too bad (though doing it 4-5 times gets a little old), but then I have to gather updated plugins (something I may not have to do much longer, since the latest version of WordPress seems to have an integrated updater.
The real PITA though is updating my theme. A few years ago I decided to use K2, which was under active development. It’s still under active development, and it seems like each time I update WordPress, I have to update K2 too. I’ve done some customization (inserting some AdSense code, and integrating code required by a specific plugin, and so I have to propagate my changes to the themes for each blog.
Wish me luck. I think the last time I did this, I only updated a subset of our blogs.