You have the free time since you're not tinkering, right? :P
You're talking about problems that "piss you off", whereas Linux has problems that not only piss you off, but completely stop you from being able to do what you need to do.
It's easy to talk about these things in abstract terms, but frankly I've run across two problems with Mac ever that I actually had to fix in order to do what I needed to do:
1. Get "gcc" to point to "gcc" instead of clang.
2. Get Valgrind to work (which problem is admittedly still not solved).
The problems that I've had to fix in Linux often start immediately upon booting up for the first time and attempting to connect to wireless, and end with me emailing documents to a Mac to print them because I needed the document printed within an hour, not after 8 hours of tinkering.
Upgrading macOS and Xcode is a pain, especially with Homebrew and Macports. You'll have to recompile most of your installed applications and it's all managed with a hacked together package manager. Virtualenvs won't survive updates if Python is sideloaded because of linking issues. It's just a mess.
The result is having to spend an unknown amount of time fixing things that upgrades break on macOS, meanwhile upgrades on Ubuntu just work.
Then I stopped. These days rarely go beyond setting terminal font (I built mine, so it's only fair I play lab rat with it) and some Emacs settings. The effort spent in customizing every detail of every app is very rarely, if ever, recovered.
I feel a bit embarrassed I recently added overline support to tmux because I wanted proper overlined status lines on my terminals. In my defense, I did it for fun, not to improve my performance.
I suspect what you mean when you say "it didn't work" is actually, "they didn't like it", which is actually not the same thing. I see a lot of people saying they didn't like things on Macs, not a lot of people saying things didn't work on Macs.
Unless we're talking about 15+ years ago before Linux had driver support for most stuff, or trying to like, just install Mac OS on an unsupported platform without hackintosh workarounds.
I transitioned from GNOME to i3wm quite a while ago (after like 15 GNOME upgrade cycles, where I always had to figure out what changed, and fix what broke), and it was basically a day or two figuring out what I want and inventing/learning the shortcuts (not fulltime days, mind you). And maybe 2-3 instances of "this feels stupid, how can I improve it".
Certainly orders of magnitude less time than I ever spend making Windows do what I want on every damn re-install.
Now that I had my configs, I just copied them to all my 4 or so desktop/laptop machines, and it's such a timesaver. i3wm being ultra stable, there's no ongoing maintenance.