If I have to read doc or something online so that my OS stays usable, it's already game over
In return you'll never need to update a Debian release name in sources.list, click away a nagging update prompt, wait for a double-reboot cycle for some registry changes, or anything of the sort.
Yes, you will need to understand what's on your system to know what news is relevant for you. You automatically will because you set it up yourself.