Besides opening up a sales channel, is there SOMETHING that can explain what the right way to license Office + Windows in a 50-employee business?

I've gotten by for SOOO long with samba + OSS, and our main stack is OSS, and have remained on the up + up with licensing. But with CAL's, Domain Controllers, File servers, etc, etc -- It seems to get so obnoxiously expensive fast --- for the only benefit of entrenching yourself to Microsoft tech?

Given that I have to maintain a fleet of 40-50 Windows devices, Along with Samba 4, is there any good tech stack OSS or otherwise for managing all that?

If the company only has 5-10 employees, it is pretty safe to assume they will not have a dedicated IT function who would worry for them about volume licensing, domain joined systems, etc. They likely just buy a laptop on Dell's website which comes with whatever version of the OS Dell tells them is good for them.

It's still a hard sell. If a machine comes with Windows [Version] Home edition, there are business reasons to upgrade.

If you buy a business machine with Professional edition, it already services all the business needs.

I used to have good reason to push volume licensing when Enterprise was necessary to get Bitlocker.. but now there's very little business reason to do so.