I have looked around and have not found many opinions on if it is important to update your R software as soon as a new version is released.
Any opinions would be welcomed!
As with any software, you should carefully evaluate what is included in any new release. If the release consists only of bug-fixes, it is usually expedient to install it as soon as it is practicable for you to do so. If the scope of the release is more expansive -- new features, etc. -- you should review the release more carefully.
If you're in the middle of an important project with a killer deadline, it's quite reasonable to wait a little while before applying any update.
Also, you should as a matter of routine re-run a selection of jobs, that you know the answers to, in order to be sure that the answers are still the same. "No, mistakes of this nature don't happen often, but they do happen."