I agree. I'm really baffled by the Rust community pretty much standardizing on MIT license. People laugh at "Rewrite it in Rust" which I think is a good thing but completely ignore the whole "strip users of their freedom" that is coming with it one day.
There's no loss of freedom with permissive licenses.
The eventual users of the hypothetical commercial OS lose their freedom. (Or don't get their freedom, depending on your point of view.) Permissive licences grant users freedom, but don't preserve those freedoms in derivative works, so the original work can end up helping derived software disrespect users' freedom. For those who believe that users' freedom should always be respected, this is a very bad thing that needs to be avoided.
On the other hand, the scenario you describe where everybody wins is already proven to work with the GPL since that is the Linux story. That is the point of it - when everyone cooperates we all win.
There are already plenty of de facto proprietary forks of Linux. Practically every embedded SDK comes with one. Yes they have to publish the source because of the GPL, but they never bother doing that in a form that helps getting any of the work merged into upstream Linux. All those vendor-specific forks end up stuck at some random old kernel with dozens of known issues, effectively abandoned. This has effectively ruined the ARM landscape, and of the end-user visible SBC choices only RPi has a decent reputation for working well enough with upstream Linux devs.
Submitting your changes to upstream Linux is a competitive advantage. (With the trade-off that you can't hide your sooper sekrit hardware designs as well.)
Google/Android has put in a huge amount of effort to drag the hardware vendors out of this pit where they get stuck on old kernel versions...
It was specifically GPLv2.
I feel the GPL lost a lot of momentum with FSF's GPLv3 push.
Linus was publicly against it. Not only for Linux, but generally and philosophically against it. I presume a lot of others felt the same too.
In theory you could continue using GPLv2 for new projects, but given that FSF had basically deprecated v2 in favor of v3, it seems that the momentum for v2 just slowly died out, and v3 was too controversial to gain widespread acceptance.
Without a GPL default, the developers who didn't want to get too deeply involved in ideological questions probably just adopted MIT as the new default.
It ensures everyone benefits from improvements, not just users who are willing to pay bigco.
Even if it "takes off", how can a commercial entity extinguish a person's motivation to keep building something they want?