Every year, Jason Snell of SixColors does a round-up of Apple via a scorecard from various Apple pundits, the interesting takeaway was Catalina was a bad move. I always find this interesting, as an (exceptionally) minor one myself. Gruber has some of the most damning feedback.
If Apple has somehow determined that typical users need these sort of permission alerts, fine, but there should be a single switch for expert users to toggle to effectively say “I trust all of the software on my Mac”. Call it “Pro Mode”, call it “Developer Mode”, call it “Expert Mode”, whatever. But I don’t know a single expert Mac user who is not seriously annoyed by the heavy-handed security design of Catalina. Not one. Every single expert user I know is annoyed. That is a bad place for MacOS to be. MacOS 10.16 needs a serious course correction to fix this, and if 10.16 goes the opposite way — growing even more heavy-handed in restricting professional Mac users from just using their machines as they want and expect to — I genuinely fear for the future of the Mac as a platform for serious computer users. Which is crazy considering that Apple just unveiled Mac Pro workstation hardware that can cost upwards of $50,000. - John Gruber, My 2019 Apple Report Card, daringfireball.com
Catalina marks the most significant regression in macOS functionality since Yosemite, with glitches aplomb. I've put off upgrading on both my Mac Pro 2010 and my MacBook Pro 2017 as I just didn't want to deal with the headache. This is only a delaying tactic as inevitably, I will be required to upgrade. While 10.14 was controversial for many users as it switched to Metal, it had to happen as OpenGL was a dead-end, and it made little sense for Apple to put it's GPU fate again into another OpenSource project when it had its own API.
Catalina's security conscience, as a friend pointed, was a bad pattern when Vista adopted it. It effectively trains a user to suffer alert blindness, and it actually encourages power users to disable SIP and turn off code-sign verification. Apple still refuses to introduce basic detection for when its walled-garden is inevitably scaled. All it can do is revoke certificates. This isn't very good. Having used Windows 10 and tried to use sketchy utilities like a save-file editor for an older video game, I'm impressed how reliably Windows Defender rejects applications. Granted, I'm not much of a Windows 10 user, so perhaps I'm skewed by ancedotalism but fact remains: Apple has no analogous feature to Defender. It still operates primarily on security-through-obscurity and user-hostility to promote its own app store.
Then to add insult to injury, Apple removed 32-bit Application support. There's plenty of older media utilities that'll be forever sealed to a 32 bit OS, I own a few audio utilities, and there are Steam games I have that aren't Catalina compatible. 32-bit executables weren't holding anyone back. Windows 10 has no plans to phase it out. Catatlina is exceptionally low on meaningful updates, sidecar being one of the big sells but strangely locking out hardware that is still capable of running it.
The OS has always been the catalyst for all my Apple purchases. I prefer macOS to Windows/Linux, and I prefer iOS to Android. I'm pretty sure any working professional doesn't by Apple products because of their hardware merits alone as I've yet to read of Windows users buying Macs only to run Windows full-time. You can make a strong case for the iPhone and iPad as it's indeed best in class. The Mac? Much less so. Apple is playing a dangerous game with macOS.
If I were scoring Apple's properties: the Mac line-up would get a C+, as most of its laptops still have goofed keyboards, the prices hikes have been rough, the iMac Pro is stuck. The Mac Pro is beautiful but priced out of reach in a way that feels out-of-touch. For its software, a D. iOS 13 was painful in its first releases and Catalina marks regression in functionality and bugginess. Also, there's been some idling on Logic and Final Cut Pro, although its new services all seem solid (Apple Arcade, News, TV+) and yet it's biggest win, Apple Maps landed in 2020.
I'm keeping my fingers crossed with Apple's renewed interest in "pro" comes OS upgrades and software worthy of its high priced hardware.