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This depends on the type of case and how far into litigation the case has gone.  Once a complaint is filed in court (i.e., publicly available), there are significant ethical limitations on a lawyer's abiliy to "silence" by agreement the participants as to matters in the public record.  If litigation has not yet occurred,  an argument can be made that there's more flexibility. 

This depends entirely on the wording of the agreement. 

If the person defamed is a non-public figure, defamation is the negligent publication of an injury-causing and false statement about a person.  "Publication" means communicating the statement to any third party. 

It depends on whether the language of the confidentiality agreement binds him or not.    If there's no term in the agreement requiring him to remain silent, he clearly did not violate it. 

In the case of a private person bring a claim against an alleged defamer:   you prove (1) that defendant made a statement, (2) that the statement was false, (3) that the statement is one which tends to injure a persons reputation or standing in his/her personal or business community, (4) that the defamatory statement was made negligently, and (5) that it in fact caused injury.   Usually this is done after a period of "discovery" whereby the lawyer representing the plaintiff has the opportunity to ask the defendants/alleged defamer questions under oath and to obtain documents relating to the event.   Discovery provides a primary source of evidence in such a case.

Very hard to say.   It depends again a lot on the wording if the agreement.  However, if a defamation action is filed, the confidentiality/non-disclosure agreement  would probably not provide any shield against discovery of the underlying facts.  In other words, these private NDAs may not prevent the vicitms of the alleged defamation from making allegations in complaint about how exactly they were harassed (assuming, of course, that they were).    In order to prove the defamation case, they would have to allege/prove that Mr. Cain's statements were false - i.e., that he did in fact sexually harass them. 

Strong sexual harassment cases can produce settlements much larger than $35,000.   However, many people don't want to live through the ordeal that is litigation.  Defenses in such cases include allegations that the plaintiff is lying.  Who wants to be publicly called a liar and subject themselves to an assault on her character?  It is conceivable that a good case could be settled for  that sum simply because the victim does not want the disruption that such cases frequently  involve. 

When you talk about a persons "right of speech" you're referring to the party's federal and state constitutional rights.  Those rights prevent federal, state and local government authorities from abridging free speech.  They do not prevent private parties from freely entering into agreements to refrain from making certain statements. 

Again, very hard to say without knowing more facts about the underlying events.  Were the harassment allegations against him well founded when they were made in 1990s?  If so, there's a decent argument to be made that Cain is making false statements about his accusers when he says that the accusations were false.  

That's a question of political tactics.  I'll defer to others.

This depends entirely on the terms of the NDA. 

She could, theoretically, be required to pay damages or to repay the funds she received.  The terms of the agreement will dictate what recourse the non-breaching party has.