Hello,
Great question. I tend to only upgrade when I actually need to, for instance if there is a security bug that has been fixed, or if a module that I wish to use requires the absolute latest version.
Whenever a new version is released I always wait until other people have tested it out as there is always bugs in the very first release of a new version. - The best place to check for this is the discussions in the main DotNetNuke forums. - I tend to wait when upgrading until several point releases have been made ie. 4.6.2
In your case I would hold out for a while.
If I decide to upgrade, I download the entire site and install it on a localhost installation. I then perform the upgrade on a localhost installation to double check if any errors occur. Once I am sure everything is working correctly I then upgrade the live site.
You can look at tutorials related to this here:
How to upgrade DotNetNuke from v3.x to v3.2 on a live website(same principles apply on the later versions)
How to Upgrade DotNetNuke v3.x to v4.4.1How to backup a live hosted DotNetNuke website and restore it to a localhost installationWhatever you do, make sure you create a backup of your live site before attempting anything!
Thanks,