I have been getting really worked up about upgrading all my blogs to WP2.5 as it is such a painful process. So while looking for something else, I came across this plugin that should save all the pain.
It is the WP Automatic Upgrade Plugin. Download and instal this and you won’t ahve to do any more manual upgrades. Be sure you back everything up before you do an upgrade.
Another thing, this plugin I found a while back is quite helpful in checking things out before you upgrade. Have a look at that too, WP Upgrade Preflight Check.
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