Moved my sister to Ubuntu a while ago aside from the occasional support call everything works quite well.
As for my mom, I sat her down way back and told her she needed to move off of Windows XP (support was running out). I explained to her that she could learn Windows 7 and eventually 10 (8 was already a known dud by then) or she could switch to a “Traditional” desktop paradigm that resembled XP closely where she’d only had to relearn once and then keep running it forever, so I moved her to MATE.
While most issues she had with incompatibilities could be solved (and often remotely by me just via ssh) there was one MFP that just wouldn’t scan properly (I’ve scoured the web for guides and sane drivers etc.) in the end I set up a Dual boot Windows (with a nice "switch to Windows " script right in the pinned apps) just so she could scan from there (scans automatically saved on a NAS share that was also available in Linux so she could use the scanned documents there). These days the MFP died and she got a new one that will actually scan in Linux but I kept the dual boot just in case (though I doubt she ever uses it).
I’m in the lucky position that I always could work with Linux. I was working with people that couldn’t be bothered to run Windows on their Desktops (administering mostly Linux Servers anyway). In my first job we had a “Standardized” Fedora desktop that was actually attached to our AD so you could log in at any desktop with your domain user. However we did have internal tools and some software requirement that only were available on Linux meaning everyone in our department had a Windows VM for using those tools (kinda overkill but ok). My last job we didn’t have any standard other than the system had to be encrypted and had Eset installed other than that we could set it up he was we liked.
Could I work with a Windows desktop? Sure I’m on the Terminal sshing into systems 98% of the time anyway but at the end of the day I love to simply be on Linux having a workflow I’m used to.
Regarding Office I was just using Office online for anything that needed it.
Getting Linux Systems into AD is possible (but of course requires cooperation on the side of the IT department)
Proxy and VPN should mostly be doable (but of course might not be able to be deployed via Group policies)