I think this is more a case of stubborness.

He paid a lot of money for x things years ago & is going to milk them for all they are worth until they no longer work, but each to their own.
Been there, done that. I paid an arm and a leg for a Cinema4D 6 license with all the bells and whistles, continuing the ever-increasing upkeep until version 9 with all modules. I just could not afford it anymore as an indie freelance at that point.
Switched back to Lightwave, but Newtek pretty much destroyed that product into oblivion. I decided to try Blender, and have not looked back since. I support the Blender Foundation with a small monthly donation.
Blender 2.8x is excellent. It is on par (and beyond in certain respects) to its commercial siblings. I can't see any benefit of using old 3d software when Blender is available for free, and leaves those older commercial apps in its dust. And the usability problem is a thing of the past with this version.
A free version of Davinci Resolve will take care of most video editing.
My advice is to let go of ancient versions, and look into some of the open source options or inexpensive newcomers on the market. Krita is free and excellent for digital drawing/painting and frame-by-frame animations. Affinity is inexpensive, and a good replacement for Photoshop, Illustrator and InDesign (mostly, with some papercuts).
There really is no need anymore to invest in expensive (rental) software as an indie dev/team. It is quite amazing what options are out there right now. The market has changed.