I tested all recent versions of MacOS on a MacBook Pro running Yosemite (10.10), and
finally the version which was not causing too many applications to fail or too many
use problems was:
High Sierra (10.12)
You can check if your MacBook Pro will run it without problem here:
https://support.apple.com/kb/SP765
You can dowload it here: http://updates-http.cdn-apple.com/2019/cert/061-39476-20191023-48f365f4-0015-4c41-9f44-39d3d2aca067/InstallOS.dmg
Due to the problems I got when testing Catalina and Big Sur, I advise you to make,
before testing any upgrade of MacOS, a serious backup, and even verify it.
For example, Carbon Copy Cloner: https://bombich.com
will let you make a bootable copy of your running system and this is a huge time saving
when you come to check any MacOS upgrade: you can boot immediately your copy and check everything
is working as it should.
My personnal experience is that among the most recent versions of MacOS, High Sierra is one of the
best in term of overall quality, real improvments and not too many changes in user experience.