I would be convinced if upgrading WP weren’t such an extraordinary headache. Plugins break, critical functionality is lost–it’s a nightmare if you’re doing anything non-standard with your blog. So sure, if you run a safe and happy default setup why not upgrade now? Anything more complicated and you’re generally better off waiting.
Two oft-touted WP claims:
– WP is infinitely extensible
– WP is more than a blog; it can be a CMS too
Those claims are valid but they don’t mesh well with the whole “upgrade NOW!!!” messaging piped out through messages like this. If you want to extend WP you’re stuck chasing lazy plugin authors who have no vested interest in upgrading their work (woe be to the blogger that learns to rely on some special piece of functionality they couldn’t code themselves). And of course, plugins are usually required to make a real CMS of WordPress. It’s a shockingly easy cycle to get into: spruce up your WP install, fail the next upgrade, scramble to look for updates or fixes when your crucial plugins break, and then repeat three months later.
2.5 looks cool… but no thanks, I’ll wait a little while.