Man I still haven't even left Mojave for Catalina. I don't think I'm gonna be changing OSs until I buy a second or third generation ARM Air that comes with whatever they're calling the 2022 Mac OS.
I religiously upgraded every machine up until this same release. I never had issues, and my tenure began at Tiger. Everything was smooth sailing – perhaps because I made sure to take a backup before every upgrade which might have protected me from Murphy's law.
I am also sitting still on Mojave. In the past there were usually compelling reasons to upgrade - in terms of quality of life and performance. Catalina, in my use cases, doesn't really do a whole lot for me. I can't think of a single feature that I want aside from perhaps the standalone Podcasts app. But because of all the noise raised during the last upgrade season from Mojave to Catalina I decided that the juice definitely wasn't gonna be worth the squeeze.
So now I have pretty much decided to just cruise this 2018 MBP along on Mojave until I replace the machine entirely. If it ain't broke, don't fix it.
Might just be me, but the Podcasts app was actually pretty slow for me on a 2015 MBP, even though the phone version always worked great. I ended up switching to Spotify for my podcasts. No other benefits to upgrading I can remember. It makes your security settings a pain to deal with for a while after you upgrade. I didn’t have any 32-bit apps I’m missing so I wasn’t affected by that. The one cool thing about it is Sidecar if you have an iPad and Apple Pencil to use as a drawing tablet, but I don’t.
Problem is it's broken from a security POV. This Big Sur release of course has a bunch of security fixes and it's not clear when/if they'll get backported to previous versions.
32-bit apps. I have 32-bit apps where the developer is either gone or will not update, thus if I wish to keep using these I have to stay on Mojava. This applies to four Macs which will likely never move away from Mojava.
We've got a old legacy multiplatform app that supported OS X for years. Looked at updating it for Catalina, was going to be a massive amount of work, since Apple also killed XWindows and updated OpenGL in some breaking way. Decided it wasn't worth spending months on it.
Still get a regular trickle of emails from schools complaining about it. I tell them to call Cupertino.
Catalina didn’t kill XQuartz, nor did Big Sur. It still works fine, though it hasn’t been updated in 4 years.
It also did not break OpenGL, only deprecate it. macOS is still stuck on a many-years-old version of OpenGL, but what worked in the past continues to work. Even Apple Silicon Macs will support it.
64-bits have been around for few years. This means developer did not have sustainable income or is not compatible due to missing API (old Carbon times). Sooner or later you will need to move on. I am also on Mojave but booting to Big Sur to build for M1 with Xcode 12 is pain in a.
One of the reasons given for the change to the California theme was that they wouldn’t be running out of names any time soon. So this will keep going for the foreseeable future.