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.
Perhaps there exists some subculture of folks that delight in having to read a set of articles published in the time between the last update and today before they do so again, but I have never encountered it.
It's honestly incredibly low-maintenance. You just have to spend a relatively long time setting things up first.
Yeah.. once I did a normal upgrade and it fucked my whole system. I asked for help and I was told that exact sentence "read the mailing list, it was announced". Thanks, but no thanks.
Any changes that could be problematic are announced on the site and the arch-announce mailing list. It's really not a matter of weeks. I've gone many months without updating, without any problems.