One thing that drives me nuts is the way you get a security popup when you're working in a terminal. So you're ssh'd into a mac, you try to do something (like xcodebuild or whatever), and then it just sits there doing nothing while it waits for you to put in a password on a window you can't see.

It's not exactly new in Catalina, but it's worse. Apple just does not even think about the fact that you might want to do things remotely or automatically.