• on software ownership
Stallman is always advocating for users who install software onto their own computer. The software freedom that he advocates is all about the user to control their own computer. The software ownership that Stallman is referring to relates to the people who distribute software and also forbid the users to practice any of the four freedoms of free software. Linux and Qt have software owners by definition; the fact that Linux and Qt have owners is not the point, the point is that the user is permitted to practice all four freedoms for the cases of Linux and Qt software. The free software manifesto exists to the antithesis of the people who distribute software and also forbid the users to practice any of the four freedoms of free software.
• on the failure of the GPL
The GPLv3 is a very simple license when you can understand the spirit of the GPLv3 preamble. All the legalese exists specifically for people who do not understand the spirit that's expressed within the preamble. If you want to get tricky by finding a software conveyance technicality that contradicts the spirit of the preamble, the GPLv3 is specifically defined for these people who desire to contradict the spirit.
The GPL3-or-later clause is specifically an expression of convenience. The reason why a software conveyor to use this clause is because they agree with the spirit of the FSF and GNU who writes the licence. There's no mandate for a copyright holder to declare this clause.
I need to make a distinction here regarding the GPL: it is not necessary to licence your work to be GPL when you integrate and distribute other people's GPL works into your own. The actual requirement is that the licensing for your own work doesn't contradict the GPL. The easiest way to ensure this is to distribute your software under the GPL, but it isn't the only way to comply with software conveyancing under the GPL.
The GPL does not corporations from stealing GPL-licensed code and integrating it into projects. The GPL does not harm developers of non-GPL-licensed FOSS software.
• on the failure of FS culture
The guy is conflating the principle of "users must control their own software" with the practicality of "it is expensive and often unfeasible to hire software developers to modify the software on the computer". These are distinct matters that must not be conflated to be the same thing. The matter of software freedom doesn't deal the financial burden and time burden of tinkering with source code. The principle of software freedom is that users have the default freedom to do it, no other explicit permission is needed from any software owner.
• on the failure of FS with cultural relevancy
He doesn't like the strict adherance to ideological consistency. He wants the FSF to weaken their own principles for the sake of "fitting in with the majority of people", people who oppose the FSF principles.
The quality of GNU software isn't a high ideal for the free software movement. The highest mandate for GNU is simply to exist: it is a platform to allow users to escape from proprietary software. It's good that other free software exists, there's no requirement for GNU to "be the best out of everything".
Stallman does his activism work for FS because he knows what he's talking about. Anybody is welcome to take on the burden of advocating for free software; there's no requirement for activism to be exclusively about Stallman.
* Where Do We Go From Here?
The FS movement is a failure when you judge it based on principles that the FS movement doesn't care about. "Real men don’t attack straw men"