That's not how the open-source movement works. You can't start excluding people based on usage you don't like. If you do that, you're explicitly not following open-source ideals.
Apache license, mozilla license and GPL has provisions that terminates the licence upon the initiation of particular lawsuits. The most common ones are Patent retaliation clauses. This is nothing strange, and has existed for a rather long time. It would not be a stretch to expand this to trademark lawsuits.
It's not at all - that means you're ceding many rights to the authors of the software. Suppose I want to use open source X from Company Y, and they had that provision. Then I find that Company Y is pirating my software, slandering, hacking our servers - if I sue them, I now lose my license?
Why would I build on something that lets the owner act against me with relative impunity (assuming the software is something critical)?
I considered that and I'll admit that I was being a bit lazy with my comment but I think it could be written in a reasonable way. Perhaps a license fee attached to any failed legal action. Or even limit to certain types of legal action.
We can't even be sure that Python-the-company is using Python-the software, so ...
Furthermore, I think the problem is not here, the PSF clearly made a mistake by not registering the name (it's not a matter of 'bad law'). If we apply your solution, then it would mean that a company which does not use Python can still ask to register a global trademark named on the term.