There have been many years of cautions about Mac OS upgrades from many folks. Some. eg Lloyd Chambers, have been more vehement about it than others. I confess, even though I'm among the cautious, (still on Mojave),
I wonder how some people seem to have so many problems (especially with Catalina?) whereas others seem to glide along. They do the upgrade and somehow, life goes on. I'd love to hear from those more savvy about why this seems to be the case. The obvious answer is "other software," but I'm mainly interested in Lightroom Classic and Photoshop 2020, and, of course, my beloved Epson 3880 printer. With the impending chip switch, I too am wondering if it's time to trash my Mac Pro 2013 "trashcan" and get something new before the inevitable confusion around the new chips gets going. At least with an iMac 2019 I could "revert" to Mojave assuming such a machine would ship with Catalina. I don't want to jump out of the frying pan into the fire though.
Opinions and experiences welcome.