So let's say you have 10 Million miles. You want to convert them into actual cash. How would you go about it without violating any of the airlines T&C's?

Could you transfer these miles into another program where they would be redeemable for cash?

Could you transfer them into another program (like a hotel program) with less restrictions about barter and selling awards?

Could you use them to purchase resellable goods or services?

Even if you were going to take a big hit in the mile value, the devaluation.

This is a hypothetical, but the basic question is-- what's the path out of miles into cash, at any legal price, and then, can we find the best price?

One idea that came up for me-- let's say I own a company. I have employees. I fly them around. I have 10MM Amex Points. Can I use the Amex points to book my employees travel on reward tickets?

Now let's say I don't own the company, can I perform that service for the owner without selling him the tickets for business purposes?

You can see where it gets complex. The point is to NOT violate the T&C's, not to ANYTHING shady, but see even if at big loss what is a path back to cash.

Interesting........