[engineerDave]

All this talk about "I need Office to be Office" and no one mentions o365 online? Which works just fine on Linux. Also label printing seems a common issue but no mention of support of old old old legacy hardware that still works perfectly fine. For instance, my scanner which still works perfectly fine but won't work on Windows or Mac anymore works just fine on Linux because of the legacy driver support.

Not a business owner. Programmer who was a sysadmin in a former life and is familiar with all three O/S and a few others, e.g. embedded firware, etc.

In every organization, there is usually one app that ties a particular user to a non Linux OS, e.g. usually it's Adobe products, sometimes active directory, sometimes it's because "we have Access and it does everything we need it to and no we don't know what it does anymore", we need X software for X platform because skillsets and training.

A lot of lawyers would still (and some still are) be on WordPerfect if they could be, some accountants are probably still on FoxPro somewhere out there, but IME most users just need a Chromebook and a subscription to o365. Maybe ChromeOS Flex is an option for them?

If they have custom needs then they IME don't need much more than a CSV file and a simple ruby script that can import their label addresses from a CSV and spit them out to the printer a la ruby's Prawn.

The argument for training loses weight when each version of Windows and macOS changes fairly drastically you have to relearn with each major upgrade. Usually forcing hardware upgrades too well before the machine has stopped being viable. Whereas learning Linux once and that being all you have to know forever and can blast onto any machine, copy your files over, run your setup flat files or whatever you use to bootstrap your setup and IMO the training argument should push more to Linux but it never will for one simple reason. Support. If the manager can't offload a user needing help to support then all bets are off.