If you have a newer version of Windows, I don't understand why the automatic update isn't enabled?
With that function enabled, at least the critical updates would always be done.
For non critical updates and driver updates, it's still up to you to check the update site.
Once a week is a good suggested frequency.
Besides, it's fun to update. especially if you have a slow dial-up connection.
Your operating system, virus program and, your firewall program should always be up to date.