The problem is Linux is, as he puts it, hard to learn and hard to master. So once I've gone through the learning phase for fun and learned what to do, I really want to just keep using it and not have all my hard work undone at a whim.
Perhaps ironically systemd is one case I would point to as being an acceptable breakage. The software itself definitely fulfils the license's promise of "NOT FIT FOR ANY PURPOSE", but as an idea it's mostly sound. It suffers from bad design in that e.g. it has no concept of "ready state" so there is no way to express "The VPN service needs the network to be online" and "The NFS mount needs the VPN to be connected"; thus it also has no way to express "you must wait for the NFS to be cleanly unmounted before stopping the VPN" - only "you must execute umount before tearing down the VPN (but without waiting)". Similarly if you have a bind mount you can't make it wait for the target to be mounted before the bind mount is executed (i.e. if I have an NFS mount at /mnt/nfs/charlie and bind mount /mnt/nfs/charlie/usr/autodesk to /usr/autodesk, I could find no way to make systemd wait for the NFS mount to be done before bind-mounting a nonexistent directory - contrary to the man page for /etc/fstab it executes all mounts in parallel rather than serial). All that said, you can work around it by sticking to bash scripts, which is the good part - it still retains a good bit of the old interface.
The problem really comes when a completely new way of doing things is invented to replace the old way, e.g. ip vs ifconfig, nftables vs iptables - now you have to learn a new tool and keep knowledge of both the new and old tool for a while (about a decade or two) until the old tool has gone completely out of use in every system you administer.
This was the kind of thing we used to make fun of Microsoft for in the '00s. Every year a new framework replacing the old framework and asking you to rewrite everything. In the end people just kept using the Win32 API and Microsoft actually kind of stabilised their churn. Now Linux is making the same mistakes and alienating existing users. I'm not sure how things will play out this time, I just gave up about ten years ago and run Windows on my PC. My worry is that the Linux world will get stuck in a cycle of perpetual churn, chasing the One True Perfect Form of Linux and repeat all the same mistakes as Microsoft did twenty-thirty years ago except without the massive funding behind it.
Or put another way, I can no longer trust Free Software. The people writing it have shown over and over again that they do not respect users at all, certainly much less than a commercial vendor does. Idealism trumps practicality in the Free Software world.