I'm pretty sure Tim isn't going to bother to respond to you, so I will. I also disagree vehemently with Tim about lots of things, so I can't defend all his points. But some of them deserve a better response that you gave, if one can be made; or deserve acknowledgement that there's a point.

(0) The constant antagonism detracts greatly from the mood of this reply as a set of serious answers. Not really the best look. But, fortunately, you have been pretty good at not actually relying upon all the character attacks to make your points, so I can just ignore those and address the substance.

(1) Tim's point is completely untenable, but somehow your answer utterly fails to point out the untenable part.

You give the answer to this one later on: we already have robust ways to determine intent in cases where we decide it matters (e.g. if there is racist intent behind some action).

But you don't give that answer here. Your answer is terrible because it focuses so heavily on antagonism that it can't even articulate a clear point. Furthermore, Tim explicitly rejects a position ("no one should seek to make another person feel bad because of their racial identity") which you turn around and claim he accepts ("decent people can agree that that is not carte blanche to engage in willful racial attacks on students...can’t say that I’m surprised to find you outside that number, Tim").

You were like five meters from the goal with no goalie, and somehow you kicked an own-goal instead of scoring. Good grief!

(2) You nail this one. Using the principles of the founding of the country to continually work towards a more just society pretty much blows the idea that the country is "inherently racist" out of the water, much less the idea that there's no way to teach it except as inherently racist.

Five meters out, and this time you kicked a solid goal.

(3) Tim's core question is, "might the fear of being sued intimidate teachers". He doesn't say that they might lose, which is what you're arguing against. The point is that facing a lawsuit is intimidating enough. And it doesn't take the entire community to agree--a single outraged parent can do it.

Tim's point stands completely unanswered. You don't even get a foot on the ball.

(4) Tim's point is that there is no way to make the history of the South unobjectionable to both black and white students. This might make teaching history, according to the anti-CRT laws, actually impossible. You answer with a diversion (attacking postmodernism), then use the rest of the answer to try to address a different point which is that the current system isn't fair in how it treats discomfort.

You don't even look in the direction of the ball. Are you even playing the game?!

(5) Tim picks out a particularly unsavory group and tries to generate guilt by association. You answer that you will have no part of it, which is exactly fair, because guilt by association is a logical fallacy.

Goal! Tim's point is completely answered. Should never have been asked.

(6) Tim again makes a point about not being able to make things pleasant for everyone, but this time he's focusing on students vs. students, so the issue of the law being unenforceable doesn't apply. You engage with the answer, from the opposite perspective (Tim thinking that currently, black students get the discomfort while white ones are spared; you thinking that white students currently get the discomfort while black ones are spared).

Since no evidence is offered by either side, the issue stays contested. Some good footwork here, no real motion.

(7) Tim picks out more racial groups and events, asking if the events should be taught, or not, because of "fear it might provoke animosity towards their children or instill guilt for the actions of others". Key word here is fear, because we haven't established that the possibility of a lawsuit won't have a serious silencing effect. You miss this key part of the question, answering instead that it ought not instill guilt because you can just not talk about it as if everyone in some group is responsible for the actions of a few.

Maybe you get a foot on the ball here, but not control of it. Without addressing the difference between what ought to be and what can be feared, and which is enough to trigger lawsuits, and how hard teachers might try to avoid any possibility of a lawsuit, you don't really have a good reply.

(8) Tim wants to discuss racial inequalities in schools. You dismiss the whole topic as something that just shouldn't come up that much. It's a fair point--Tim should have argued for it being necessary.

Good save--you win this one, but only because Tim took such a terrible shot.

(9) Tim keeps wanting to discuss inequalities! You shut him down again.

You win again, for the same reason.

(10) Tim wants to focus on how bad things were in order to appreciate the progress we've made. You reject the point--the issue is how things are framed now.

This is a weird move. Tim's point is absurd on the face of it--you can appreciate a great deal of progress with out dwelling on how bad things were before. Give a few hints, leave a lot for the imagination, focus on the positive But rather than use this approach, you let him get away with the bizarre unjustified claim and focus the attention instead on the endpoint, which Tim didn't here quite say ought to sound really bad. Nonetheless, it does answer the point, kinda indirectly, but plausibly.

It's a scrappy mess, and the goal goes off the defender, but you score.

(11) Tim wants you to stop using MLK's most famous quote, apparently, and asks if you've read his other stuff. You counter that it's the right quote because people agree with the vision of racial harmony exemplified by that quote. Completely fair point.

Tim tries to clear the ball and only bounces it off you into his own. You win.

(12) Tim gives two other MLK quotes and asks if they're okay to teach. You complain that they're 50 years old. Um, yes? That is why you'd teach them as history? Which we are talking about?

You walk off the field while the clock is still running. Tim wins this.

(13) This isnt' a serious question, and you don't treat it as one, so I'm skipping it.

So--very uneven job here. If Tim was thinking all the questions were unanswerable, this clearly shows that they're not. On the other hand, if you were thinking the questions were all answered, well, also, no. I score it 6-5 in your favor.