Ubuntu installs upgrade well in my experience, unless you add weird and outdated software from external sources. A bit like manually installing pkgbuild files you found on Github. Stuff will break in the same way when dependencies don’t get upgraded.
That said, Arch installs will break when a random library decides to update, and Ubuntu will break years later when you decide to upgrade.
Except for maybe Gentoo, Arch is the most “gets in your way” OS I’ve seriously used. You need to be conscious of stuff like your bootloader configuration, the network manager you use, and sometimes the kind of Bluetooth daemon you’re running, or software may not work or break your boot. It’s pretty easy to use if you install Arch by picking the exact same software you can also find in other distros (i.e. the Ubuntu style grub+systemd+NetworkManager+Gnome set, or the Fedora systemd-boot+dracut+NetworkManager+Gnome set). Following the Arch guide without copying a preexisting software set will make your life very difficult, as I’ve found out.