>" I bet the IRS would view the act of converting the points into cash (i.e. the redeeming and selling parts of the post) as generating taxable income."

>Sure, but is your buyer on Ebay going to send you a 1099?

Getting a 1099 or not doesn't define the tax outcome of the transaction, however. I don't give someone a 1099 when I give them a tip, but that is still income to them.


>"Donating that same amount of money would likely end up, therefore, as a tax wash since the deduction would equal the extra income."

>It would seem to me to depend on how the miles were gained. Rebates are not taxable income, so I'd argue that if you gained them from flights paid for with personal funds it wouldn't be taxable income. It could be different if the points were gained for flights taken on your employers nickle. But pmarti says "The IRS has been trying to figure out a way to tax business miles redeemed for personal travel for years without success."

True. I was making the presumption that these miles were from business-related travel where being able to convert them into cash could/would (/should?) be treated identically to getting a bonus from the company.