I’ve been using Linux on the same timeline starting with RHEL3, then Gentoo, Ubuntu, and finally ArchLinux and I’ve had to arch-chroot from a live usb several times over the last five years to fix broken upgrades*. It hasn’t been more than an hour detour each time but it’s been far from painless. I just recently had to nuke and pave a Thinkpad X1 extreme to reset KDE/Plasma to a configuration that didn’t crash Plasma randomly or kernel panic when resuming from sleep (power management was especially bad for that old gen1 model until recently and I had to build a custom thermald or something). I’ve still got a problem with a monitor not working after power save - just monitor off, not even computer sleep - until I power cycle it. Some problems are even starting to crop up on my System76 Pangolin.
A significant fraction of the software I use is installed through yay’s extra packages which do frequently require building from source so it’s not just a Gentoo thing. It’s far from as seamless (or as limited) as Android/iOS app stores.
* and not even half of them can be blamed on NVIDIA