I'm gonna address just this one. If you asked Kirk about that statement, he would say "it's because affirmative action raised that question in my mind because it inherently gives positions to the less qualified."
Without debating about that statement, which could be characterized as more of a debatable position than the above quote, it doesn't really matter what the genesis of the soundbite was: people only hear the pretty trenchantly racist part of it. And I think that's by design.
That's an attention-seeking and less-than-good-faith argument style.
Also on the "cost of the Second Amendment," he gives the example of driving and rattles off a few of the social benefits of driving and say they offset the 50k motor vehicle fatalities. But he just assumes any benefit of unrestricted gun ownership without itemizing any such benefits.
And then he reduces the argument to absurdity: "we're never going to have zero gun deaths."
And all of this was on some kind of very friendly show, not any kind of debate. The Charlie Kirk Show for the first, something else for the second, with a cheering audience.