> 1. How much is compatibility with outside users and past documents necessary?
Not an issue, document compatibility is a solved problem and any issues experienced would be minor (e.g., a missing font or broken animation leading to slightly different presentation).
> 2. What is the system management story?
Corporate "system management" solutions are entirely broken on Windows, especially upgrade and software bundle management. It actively causes more harm and security issues than it solves, and needs to die.
It's dumpster fire of technologies that get stitched on top of each other, all conflicting and ultimately training all employees to ignore all signs of malicious intervention: How do you expect a user to sceptical of questionable popups/browser hijacking/similar, when your setup involves training users to ignore cmd.exe windows popping up randomly and to always interact with highly inconsistent, constantly changing and overall questionable popups appearing at any time of day asking you to do weird things (installing apps you didn't ask for, updating, rebooting, upgrading, often with countdown timers for making decisions)?
Should you have the ill-advised desire to bring the worst and most defective parts of Windows IT management to Linux, there's a handful of big vendors providing similar solutions there. So "not an issue", other than it being a terrible idea.
I've been using chromium on Linux for years and noone has noticed. Could probably move all the endpoints to Linux without too outrageous level of disruption.
1. How much is compatibility with outside users and past documents necessary? No office application can successfully, reliably convert anything but relatively simple documents (have LLMs done better somehow?). Each conversion reduces fidelity and often integrity; send a few revisions back and forth and it can become a problem. Simply adding a small headache every time an outsider emails your users' a document - or vice verssa - becomes a big issue. Regarding past documents, some users create complex applications in Excel, for example. How much of a problem is that for these users? How will those problems be solved?
2. What is the system management story? Essential to IT beyond even 30 users is a way to deploy, administer (including configuring settings), and upgrade/patch applications en masse. Microsoft provides those tools and Office, of course, integrates well with them. There are third party tools, but they need to do much better than exist; they need to function efficiently and reliably - imagine the deployment bug implemented en masse. Are there such tools for Linux and LibreOffice?