With updates apparently sometimes crashing after being only partially applied, even the most diligent research into application-specific "will I be able to run XYZ after upgrading" might not be able to save you from having to reinstall from scratch.
This is the kind of low-quality handling of software updates that I never imagined coming from Apple.
I upgraded when it came out, had no issues, and only a few prompts. Because the machine was entirely new to me anyway (inherited MBP2016), I couldn't imagine having anything to lose. But on my older machine? Still have not upgraded. Don't see a reason to, until they've ensured higher quality.
I have the idea that there's currently an atmosphere where it's fashionable to repeat other people's bad experiences. Regardless of one's own experience.
It's basically like the prompts you get on iOS. I don't have a problem with these either.
So there really is no way to know what packages are supported. Unless homebrew has a way to check..... I've never checked to see if it has a "compatibility check for catalina" mode