There are two basic problems to address when submitting to a charity waterboarding. The first and most obvious is that voluntarily experiencing the act is not really an advanced interrogation technique. That's because there's no interrogation involved. The person being interrogated must have some real information that he does not wish to give out, and that the interrogators badly want.
The second problem is that no reputable charity will want torture money. Even if waterboarding is not a form of torture, the money raised from such an event would be tainted because the specific people giving the money want to do so out of a sadistic desire to see Hannity tortured.
Fortunately, there is a single solution that will address both of these issues simultaneously. I propose that Sean Hannity be waterboarded over the course of two days with no more than ten sessions in any given day. This is convenient for everybody because the entire experience may be lived in a single weekend. Having a single night in the mix will allow Hannity to experience some of the sleep deprivation that is also common in advanced interrogation. Furthermore, the interrogators will have a real worthwhile goal, that may even save lives. Their directive will be to obtain financial information from Mr. Hannity. Specifically, if they can ascertain his bank account numbers and passwords, then whatever assets they gain access to will be donated to charity. Any reputable loans that they can generate from his personal information may also be donated to charity.
This is a win-win situation for everybody involved. The interrogators have a big incentive to help the American soldiers who benefit from the charity. Hannity has a big incentive to not give away the farm, but at the same time, he has some small incentive to cooperate, so that the families of soldiers get something. An Al Qaeda combatant may not want to reveal information that will result in the death of his brothers. Hannity may not want to reveal information that will result in his kids not going to college.
The charity can't mind accepting the money because the person they are receiving it from is claiming that it is not torture.
Mr. Hannity, this is your chance. You have to do this the right way if it is going to mean anything at all. You can make your point in the most poignant and dramatic way possible, and at the same time, you can help the families of American soldiers.
Mr. Hannity, this is important. Please don't get it wrong. The future of US interrogations may be in your hands.