The installation process has been pretty simple since archinstall and endeavourOS. The "sometimes" happens rarely, and the forums and mailing lists are pretty helpful.
The only times when an update broke a lot of stuff for me is 1. The infamous grub update which never happened again 2. Thunderbird dropped GTK support, not an Arch problem 3. I didn't update for quite a while and had to do package replacements, which were automated by the package manager but was scary 4. Budgie and GNOME conflicted with each other. Weren't very significant