One thing you could run into with Catalina, it drops all support for 32 bit applications. They simply will not run. so if you have any old 32 bit apps they will either need to be updated or replaced. The bigger the upgrade step you take the more likely you will be to run into issue with third party apps, utilities, kernel extensions, etc. As far as general operation goes I have found Catalina remarkably problem free from the first beta release. I had more problems with the upgrade to Mojave. Both Mojave and particularly Catalina introduce significant changes relating to security and that can be annoying until you get used to the change.

I always push the envelope, but I would encourage you to go to Catalina. You will have a bit steeper learning/re-learning curve but you will be in better position to then go on to MacOS 10.16 when it ships next fall.


"All you've got to do is own up to your ignorance
honestly, and you'll find people who are eager to
fill your head with information"
--Walt Disney