I had a rough day yesterday. I had 15gb free space when I started the Catalina update, but it failed with an 'out of space' error. The system was left in an un-bootable state. I had completed a fresh Time Machine backup just before starting the upgrade to Catalina, and so I tried to recover from that. That process also failed, with an error that I didn't understand- something very general sounding.
Eventually, I had to wipe my disk and reinstall macOS from the network. Oddly, this gave me a Mojave install, though it preserved my user account from somewhere. Probably iCloud, but that wasn't clear to me from the UI. From there, I deleted several large apps (Final Cut, Logic and Xcode) which freed up lots more disk space. I think I had something like 150gb free on my main system disk. I started the Catalina install again, and this time it took.
I'm so used to Apple's system upgrades going flawlessly, I guess I expected better this time through. Seems like a check of available space could have been done. I understand that sometimes it can be hard to precisely predict how much space will be required, but it would have been fine with me if Apple's engineering team took a very conservative approach to that estimating.
This is still my favorite operating system, but I think we need to work on our relationship a little bit. I'm kind of rattled by this experience.