re: Deductibility of FF miles...

There was a huge thread here in the Buzz a month or two ago about this very topic. General consensus is that the IRS would just as soon consider FF miles as something with a value of zero, much like the coupons you clip out of the paper aren't counted as income. They won't tax 'em if you don't try to deduct 'em - at least that's the IRS' take.

The airlines all have links to donate miles to charity. Those links say the miles aren't deductible, but I don't think that's for another reason: namely that the airlines are taking your write-off for you in the form of the free seat they give to the kid or family in need of medical care. In other words, if *you* got to write off the donation, the airline couldn't write off the same donation in their corporate taxes.

Whenever I've been to a charity auction and seen a free trip, it has always had a "Value = $XXX" associated with it, like all items in the auction. That leads me to believe that the donor gets the write-off for that value, and the buyer gets a write-off if and only if he buys the item for higher than that value.

Anyone who has been to a big charity auction knows that people tend to throw high values on the items they donate, and whether they ever get questioned about it by the IRS down the road is another story. It's not unusual to see 2 free coach tix in the US, with typical award restrictions, valued at $800-1000 for the purposes of the auction. You or I would probably value these tickets closer to $300 or $400 because they are so restricted and don't earn miles, but what the heck: somebody usually pays the higher value for them for the charity.