A short list of things to do before upgrading to WordPress 2.5:
• Check for plugin compatability w/ the new version — before you upgrade, identify any plugins your site depends on for functionality. The WordPress Plugin Directory is the central location to look for plugins and compatibility. Currently, even “featured” plugins such as podPress don’t claim to be ready for 2.5.
• Determine your aversion to risk — WordPress does a good job patching up security issues, but when a new version comes out the software could have new vulnerabilities that have yet to be discovered. 2.5.1 will inevitably follow within the coming weeks or months as new potential issues become known.
• Weigh the benefits — WordPress 2.5 comes with a number of new features and changes including a redesigned admin Dashboard and Dashboard widgets, customizable admin templates/stylesheets, improved tag management, better password security, a new Shortcode API, and more.
• If you’ve got a decent webhost, install WordPress 2.5 in a test directory or domain (beta.example.com), install any plugins you need, and see if they work. It’s better to break a test site than to break your real site.
• Wait a few weeks — other people will run into problems w/ WordPress 2.5 and blog, comment, and post to forums about the solutions they have. If you wait, you’ll be able to learn from their mistakes and solutions before using valuable time and resources on problems you don’t need to have.
If you have any thoughts or comments regarding your experience w/ WordPress 2.5, feel free to share.