It's taken a little while for me to take it up, but I finally broke down and upgraded my WordPress install to the latest version. I'm only just starting to get to know this version. Still, it's pretty clear that the WP team has made some good additions.
Drag and Drop Media Upload
Right away, I noticed a simplified media upload mechanism. WP is getting smarter. It can now detect the media type you want to upload and sort it appropriately. Even more interesting is the drag-and-drop functionality for media uploads. I gave the tool a quick test drive by uploading a header image, a shot of my backyard pond, below.
Anyone who spends time with WP knows that the dashboard sidebar menu structure is a bit long. On a laptop, it's not uncommon to see the menu run below the fold, forcing a scroll just to locate the settings options.
Flyout menus changes all that. It's easy to see your menu options on hover, saving the extra click and streamlining the look of the text in the dashboard sidebar.
Good question. When is something good enough? I can't really answer that question. There are security issues to consider, of course, and the newest version closes some vulnerabilities. In all honesty, the security concerns weren't enough to move me to the upgrade.
I needed a little down time on my running sites to feel comfortable with an update. The semester break created that down time for me. (I didn't want to break course websites midstream.) But that wasn't even enough, really.
In the end, my desire to create an option for users to subscribe to Page updates through RSS led me down a path that required the update. RSS Pages for WordPress 3+ required an update to my WP 3. That update went well, although the plugin page indicates that it had not yet been tested with 3.3.1. Consider this a leapfrog moment. I installed the plugin and it seems to be working just fine.