I was slow to upgrade to Catalina because I waited for the all clear from those who have gone before me. The main issue was the musical application Apple MainStage, in case there were glitches as yet unresolved. Of course, I'm not exactly running around using MainStage these days. But you never know. I'll take a decent keyboard gig if it comes knocking at my door between now and when we begin rehearsing the holiday show
(Actually, I tried to take one. Curtain Call in Stamford is doing 1776 between now and then. I never go around asking if I may play a certain thing, but I couldn't resist, especially since I know the MD. But he's playing the keyboard book and has no need for a second pair of hands.)
Fortunately, I can say that the upgrade went fine and I probably only had a little bit of detritus to clean up. It also only took an hour or so -- but I was only coming from Mojave, the OS before it. My MacBook Pro is a 2015, which is one of the favorites of musicians because it still has those little things called "ports", and the 2012-2015s are just a real stable implementation of Macs. So this one's six years old, and it'll remain to be seen how far in OS's they let it go.