I have found that upgrading to macOS current - 1 with latest update applied works well. For example I decided to update to Mojave last month, and enjoyed my High Sierra until 2019.
Having said that, I am probably not going to upgrade to catalina anytime soon (at least not until Catalina+1 macOS gets first major patch release).
Why? Well my reasoning is that lots of stuff magically isn’t going to recompile itself from 32bit to 64bit. I can probably help with that while being on Mojave.
Same. You lose every cool program that happened to go unmaintained, and iTunes evaporates. If I do upgrade, I'm thinking about a Mojave VM for maintaining 32-bit support. The problem is I feel like Apple is throwing buckets of features into macOS without ever fixing anything and occasionally randomly breaking stuff that worked, so that the net result is always worse than before.
Having said that, I am probably not going to upgrade to catalina anytime soon (at least not until Catalina+1 macOS gets first major patch release).
Why? Well my reasoning is that lots of stuff magically isn’t going to recompile itself from 32bit to 64bit. I can probably help with that while being on Mojave.