So you had someone build your blog two years ago and you’ve been happily adding new posts and pages, but each time WordPress issue an update, you ignore it until one day, you either want a new blog theme or make use of a new plugin that isn’t compatible with your old version of WordPress.
Well, on one hand, it might not be so bad but in the main, where you are a few updates behind, it can be a total nightmare!
If you keep your WordPress blog current, you can establish early which plugins are outdated, which are no longer supported and the added benefit is that WordPress apart from making their blogs easier to use and more appealing to the eye, focus on the security of your blog.
I can’t say I’m keen that they have added the auto update feature to the dashboard since clients click it and then come crying to me when they’ve broken something (like an outdated plugin) but at least, it’s a constant reminder to bloggers that it is best to upgrade.
I’m not an advocate of upgrading in a hurry though though … See my post about upgrading to WordPress 2.8. I’d rather let someone else test out the bugs and then upgrade when the bugs have been ironed out, especially when it is a major new release. That said, don’t use that as an excuse never to upgrade … it could cost you “dear” in the long-run.

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