Every other MacOS machine I work on/with, at home and at work, has either been upgraded from Mojave to Catalina, or was fresh-installed with Catalina. These machines are used by our local and remote workforces for software development, with security software, Cisco VPN, various multi-factor auth systems, anti-malware software, disk encryption, all sorts of things that test the stability boundaries. There have been almost no issues. Frankly, the Ubuntu 18.04 Linux and Windows 10 machines have presented considerably more difficulties.
I dont doubt that your long list of issues is true, but do they represent an overall picture as bad as Windows ME? Really? I remember working with ME thats a mighty high bar. I wouldnt even put Vista in that egregious category, BTW.
Now, thinking back, the release of WinXP SP2 was a big deal, it broke all kinds of things, and raised hell with all manner of apps. What was the result? Software either fell in line with the new rules or didnt. Id put Catalina in that category yeah it breaks things, but it was predicted that it would, and people had plenty of advance notice. Lots of people didnt pay attention. Surprise.
Back to my Mojave system for a moment. Will I upgrade it to Catalina? Sure, eventually, but not until I know Ive updated my critical 32-bit apps first. People, you and I included, have to take responsibility for our computers, or pay someone reputable to do so for us. Simply complaining when stuff breaks doesnt solve much.
You are fortunate that you can use Macs for work. Many places Ive seen force folks to use PC laptops. Macs are best for me and what I do, but Ive definitely been disappointed the past couple of years with Tim Cook. I wish hed forget trying to be Gandhi and spend more time sorting out his company
or better yet, leave.
He was a good bridge from Jobs, but its time to go.
My biggest disappointment isnt really with Macs or Catalina. Im not happy with the iPad and the last two iterations. Durability concerns me as I travel a lot. I wont upgrade from my Gen 2 iPad Pro until they beef up the models. This last update was a joke. Its time to refresh the OS, too. Its getting stale.
Ive met Cook a number of times. Hes a nice guy and means well, but its time to go.