We're evaluating Pro as a possible future case as we begin plans to migrate our MOTS platform from 10.3.1 to 10.6.
What I've found it that it's very much the same as going from say, Office 97 to the more modern ribbon system, or from Windows 7 to Windows 10. They do do pretty the exact same thing, but in their own way. "Same, same, but different."
I will admit that some colourful language has eventuated (it seems Pro wants you to track a process path, not give you the whole shebang in litter of toolbars and buttons, and who thought it would be a good idea to bury the explore tool so you can't navigate once a tool is active?) but as with the new Office and Windows once you get used to how it works, it actually makes more sense and is more intuitive and easy to learn.
We're recommending to clients thinking about taking up GIS that unless they need functionality in Desktop right now, they should consider starting with Pro so they're only learning one system, not two.
The one lining here is that Esri is taking on board comments and suggestions for improvements as Pro evolve. Good luck getting anything major changed in Desktop, it's pretty much set in stone now. Some ArcGIS Ideas have been kicking around for 10+ years in one form or another.