The iCloud authentication issues are the real nightmare for me. I can't tell you how many times I've been rejected using the correct email and password, and how many times I've had to use the reset function only to have it mess up again immediately after.
Now, on one machine I just habitually click to dismiss the iCloud window. On another, I've just moved it as far into the bottom corner of the screen as I can get it tucked away to just ignore it.
I'm also working on moving my web development setup over to Windows (with their new Linux support, which is excellent) so my next machine won't have this problem.
I was a MacOS user since system 9. Every one of my computers was a Mac and I never used windows for anything except the occasional game. A year ago I had to use Windows for my dev environment at work (a dotnet core shop), and I've since bought a Windows workstation for my personal dev environment and stopped using my macs completely. It's absolutely mind boggling to me that windows is now arguably a better dev environment than MacOS now that WSL is a thing, but here we are! I haven't regretted the switch at all and having access to the ocean of software for Windows has been great (minus a few things like Sketch that are Mac only).
Edit: To preempt the "why not linix" comments, I have used linux on and off through the years, but I didn't enjoy spending a large fraction of my time fiddling with the OS instead of getting work done.
Similar story to mine! I started on System 7 at my first industry job back in 1999. Used Linux exclusively on servers, and needed a personal laptop with a usable command line. Mac was pretty much my only option, since I wasn't interested in fighting with Linux's weak hardware compatiblity back then. Bought my first MBP in 2000 or 2001 and I'm still on one now.
But since I also do a lot of VR development these days, I also have a PC both at work and home dedicated to that. VR obviously dictates my platform choice pretty heavily, so moving to Windows for web stuff makes everything simpler. WSL pretty much sealed the deal, although I wish there were more VR-capable laptops that didn't look like an army tank...
Now, on one machine I just habitually click to dismiss the iCloud window. On another, I've just moved it as far into the bottom corner of the screen as I can get it tucked away to just ignore it.
I'm also working on moving my web development setup over to Windows (with their new Linux support, which is excellent) so my next machine won't have this problem.