Until the compatible plugins are available for each version, upgrading causes far more problems than it solves. I also have several of my own hacks in places like wp-load.php that need to be migrated by hand. In the meantime, the reality is that I’ve learned not to jump onto new versions, so the upgrade banners are a nuisance.
I’m sure anyone with an uncostomized install benefits greatly from one-click upgrades.
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