You should update any and all plugins immediately when there is an
update available, period.
If the plugin author has a habit of introducing new versions with
bugs, then you should stop using that plugin and find a different one
I do not see it as a good idea to introduce anything which even
remotely suggests that it is okay to not update. It is not okay.
Update. Immediately. Always.
Otto via wp-hackers
Very well said Otto, and it’s also good to know that Chrome-like updates is one thing the core team is keeping in mind. Anybody else wants to suggest telling users to not update? ;) Here’s the beginning of the thread.