It’s recent stuff. He likes a Fedora machine, but the only issue is the inability to replicate his Word docs. At this point I don’t know if Libre tools will be easy enough for him. There us nothing really intelligent happening in these files. He is not capable of handling any kind of real world complexity. So everything is going to be whatever was made super simple and easy in m$ Word.
I went through my old CD collection, but don’t have disks beyond Office for XP.