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.