1. I think it was pretty clear, but I'll try again.

There's a difference, I assume you agree, between saying I don't like behavior x and want to stop it, and saying behavior x should be against the law, and we should apply legal sanctions.

So, are you saying that you just think cancel culture sucks and nobody should do it, or are you saying that the government should take actions to stop it? I'm just trying to clarify your position because there may or may not be an actual disagreement.

2. So, I can tell my family not to support company x, I could tell my friends not to support company x, but when I start involving strangers it starts to become a problem?

When I start telling strangers that they should never go to Universal Studios ever again because some of their profits go to JK Rowling (we'll suppose I also made some flyers, made a facebook group, and am now devoting my life to this), should that speech be protected (assuming none of the speech is illegal in itself, for instance if it's libelous, or advocating illegality)? If not, why not?

Boycotts btw are explicitly protected by the Supreme Court. Which of course doesn't mean they should be, but that's the official opinion of the US legal system.

https://en.wikipedia.org/wiki/NAACP_v._Claiborne_Hardware_Co.

Regarding the bolded item: I've observed that much of the time you disagree with someone you claim (or in this case imply) that they're remarking in bad faith. Considering your position as a moderator, that's a threat and its effect is to intimidate and often shut down debate. These sorts of direct or indirect threats I feel should not be wielded by someone in your position of power quite so casually as to abuse that power in order to "win" arguments. This might not have occurred to you, but when I said I didn't understand what you were trying to ask...I didn't understand what you were trying to ask. That in the first place.

To the rest: Anyway, to your questions, I recognize that there have to be some reasonable limits on free speech precisely in order to foster more (e.g. there is a good reason why threats are not considered Constitutionally-protected forms of free speech in this country), but while recognizing that absolute freedom of expression for all is an ideal and aspiration, not something that's realistically achievable in the real world where people often disagree with each other, my aim would be to maximize it; to seek that balance that would provide the maximum possible protection of each person's right to think and express themselves freely.

An example of the kind of cultural policies I would advocate as it pertains to the protection of free speech would be the University of Chicago's statement of principles on the subject, which, put forward in 2014, has since been adopted or endorsed by 74 other American colleges and universities. Citing a history of students inviting controversial speakers (historically, leaders of both the Communist Party and the American Nazi Party, neither of whom exactly believed in such principles of free speech themselves, were both invited and allowed to speak at the university in the face of tremendous controversy and protest), the statement commits the University of Chicago to the absolute protection of the right of its students to invite speakers, including unpopular ones, as well as to the right of students to contest such invitations and protest them. As you can see in the text, while these invitations can be protested within university policy, they cannot actually be obstructed. That is the balance the university seeks to strike, and something analogous is what I favor in general for society.

As it pertains to boycotts, while they are legal and sometimes highly justified -- you have aptly cited the famous Montgomery bus boycott elsewhere -- I don't feel that trying to end the publication of J.K. Rowling's most recent work of fiction, or that of all of her works in total, is on par with the Montgomery bus boycott in nobility. To this end, while it is and should go on being your legal right, I disagree with the organization of such a boycott and feel that its purpose is immoral in that its core aim is not to contest views you disagree with, but to end their circulation by force. (You asked me before if I thought it "wrong" to organize such a boycott, and I do.) With respect to J.K. Rowling, you are not combating a real oppression here, like the racial segregation of a busing system, but rather the circulation of her ideas. That is a wholly different matter, in my opinion. It is your right to organize such a boycott, but I feel that its spirit is censorious and wrong-headed, as tend to be its real-world effects, and to these ends I favor that her publisher should not capitulate.

When we speak of "cancel culture", the key word there is culture. This is a cultural problem more than it is a legal one. That fact, however, doesn't stop the consequences from being repressive in nature. I believe you support such a repressive climate because you are a liberal/leftist and as such it usually advantages your political narrative to do so in today's America. Perhaps though if the shoe were more often on the other foot in today's Western world like it often has been in the past and often still is in many other countries, you might feel differently about the matter. I feel that a regular insistence upon "winning" social debates with brute force rather than with the coercive power of truth shows only that the latter may not necessarily be on your side.

The above, however, isn't meant to imply that I think there should be no address of the current climate in the legal arena. Taking the matter of social media culture, for example, I am a socialist and to which end I have always felt that communications institutions like these should be public property; that they should be brought under national ownership and thought of and treated as public utilities. Under such a framework, I feel that their principles both should be and realistically would be analogous to the contents of the University of Chicago's statement of principles on freedom of expression. Publicly-owned institutions, I find, are usually better about protecting freedom of expression than privately-owned and for-profit ones are.

Regarding the bolded item: I've observed that much of the time you disagree with someone you claim (or in this case imply) that they're remarking in bad faith. Considering your position as a moderator, that's a threat and its effect is to intimidate and often shut down debate. These sorts of direct or indirect threats I feel should not be wielded by someone in your position of power quite so casually as to abuse that power in order to "win" arguments. This might not have occurred to you, but when I said I didn't understand what you were trying to ask...I didn't understand what you were trying to ask. That in the first place.

Addressing your two items sequentially:

1. I can't follow this double-talk. I have no idea what it is you're even trying to say. It seems to me that you're just desperately trying to pull a justification for censoring other people's socio-political opinions out of your ass here with incoherent results. What I want is for people to be free to voice their opinions, and I mean safely. It's not more complicated than that.

Not looking to jump into your discussion with JWeinCom but I am interested in why you thought the line you bolded was a threat. I mean context is king so when reading everything before and after that line, I was wondering what particular within that line you felt threaten.  The line was in reference to this statement you made.

Just looking at these 2 sentence, exactly what was threatening about JWeinCom saying he thought he was clear but will try again.  You gave him a direct challenge to his questions and he responded that he thought what he stated was clear but will try again.  I am confused about the threat here.

I cannot respond to this in public now, as you know.

That ruling was incorrect on the day it was decided.

Yes, the way to make sure gay marriage is passed is to vote.  But not because of judges.  We should be united in favor of judges that interpret the law based on the law, not what their own opinions are.  Sadly, we live in a country where a major political party believes that courts are a shortcut to their preferred policies.  As such, we, for over half a century, have tolerated courts that routinely nullified the votes of its citizens based on their own personal views.

If you believe voting is the way to get stuff done, then vote in support conservative judges and disqualify liberal judges.

Loving was struck down based on the text of the 14th Amendment and a pretty basic understanding that it met with the wording of the Amendment at the time.  As such, it doesn't run afoul any Originalist concepts.

Obergefell is another matter.