Question for ya, why would you not go with GPO's and folder redirection? From my understanding within Windows server 2019 you can even designate 2 pc's (I would use VM's) as endpoint environment standards, using MST files, batch scripts and msi's you should be able to do almost everything. Especially with a software packager like chocolaty.

I have never done it that way, I have seen it done that way, my fear is that the GPO is going to try to install the software every time the user logs in. I am just wondering if you wrote a script to write the necessary changes to the host registry and utilized file redirection if programs would still run if you include all dependencies in the redirected folder. Would that work? Could be a fun project for the lab.

O365 can control licensing just install office on the golden wim don't activate it, or just rearm it before capturing the goldenimage.