Well, asking hard questions is a better way to gain clarity than having an echo chamber. See Bava Metzia.
Wow, that's a beautiful and powerful concept.
Maybe not explicitly "you can / should sell your points for cash", but offering "Have a ton of miles to burn? We can also work out a method to pay for the cruise with them!" certainly implied that.
You are right. This could be problematic although I'm still (perhaps naively or in willful denial) hoping that this advertised "method" didn't include selling points and no 1099.
Listening now to the Brenner interview for the first time.
A few takeaways so far.
3. AT says disputing can get you in criminal trouble as you affirming under oath that you don't recognize the charge, but an initial chargeback isn't an affirmation under oath. Of course it may come to that, but it should not be hard to at least initiate a chargeback without those repercussions.
I'm not advocating lying. But there are other things you can likely say that aren't lying. I'd suggest hiring a lawyer in these cases.
Guys, no one responded to my question about mileage buyers issuing 1099's. Can someone please do so? The answer changes the whole landscape around where this could all end up. It seems many of you on here have sold points, no one wants to chime in?
If there was multi-millions of tax-fraud, along with all the bank issues for these cardholders, they could have bigger legal consequences to disputing these charges (and if the feds start looking through the books of these points buyers servicing these cardholders involved, all the other little guys that "only" sell points could be facing consequences too).
I really don't want thousands of my brethren to have problems with the law or to have to face the tremendous Chillul HaShem in the media. Seems like if people dispute charges and banks and legal authorities start digging (although they may start digging without the chargebacks) there could be consequences none of us ever dreamed of. It also seems like people should add this aspect into their personal calculus of deciding if they want to continue to engage in any of these (admittedly profitable) transactions. If people ARE getting 1099s and paying income taxes on money earned from these swiping arrangements and selling points, disregard all these worries as its a moot point.
Do points buyers issue 1099s?