You have an iMac that is perfectly capable of running the newest macOS 14 Sonoma, but you're willing to continue using a macOS version that is already four generations old? Catalina is already showing its age. A macOS upgrade has the potential to prolong the usable life of that iMac Pro by years!
I agree with Phil0124's suggestion to check with the developers of your apps and see if they support the latest operating systems.
And I do hope you are backing up with Time Machine. Catalina is, I think, the last OS that can be restored directly from a TM backup set. That makes recovery pretty easy, actually, contrary to what you imagine.
It's your iMac so the choice is your, of course, my friend. But I'd hate to see you become one of the many who wait to upgrade until it's too late and much more difficult.