Microsoft's Windows license given for OEMs made it illegal to distribute totally unrelated piece of code on the same medium unless it was licensed in some quite specific way
That's not what it says in the article you linked to. As I understand it, the OEM's were allowed to ship BeOS in addition to Windows (or at any rate they thought they were and continued to do so). But in order to get the bulk pricing on Windows they could not enable dual boot - they instead resorted to offering instructions on how to switch your disk to booting BeOS (only) rather than Windows (only). So from that description, the limitation was not "the copyright or license forbids joint distribution"; it was "we will charge you more if you do so". And even so it wasn't a direct restriction on distribution, only on the machine configuration. So again, I really don't think the BeOS story is a close enough parallel to be relevant.
Anyhow, back to your earlier diagnosis that if some clib equivalent were distributed with the kernel there would no longer be a dividing line across which the license terms did not apply. That makes no sense to me. The line would be drawn at the API between clib and user programs. Not much difference to what we have now.
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