Some of the crap I had to do back in the late 00s to get wifi, sleep and power management even barely working on some machines felt like the hardest thing at the time. I wonder how I’d fare with those issues today, 17 years later, knowing quite a bit more about the underlying OS and working with the OS daily… I don’t know that I’d qualify that as difficult more than it was extremely tedious and a bunch of trial and error of configuration options I didn’t know anything about.
If we’re talking about modern day… not so much honestly. btrfs snapshots saved my ass a couple of times, the rare issue I encounter I just rollback and wait for an upstream fix, and the rest I typically ignore or use something else. Everything tends to run quite smooth for me as a general rule, though.