The only time I could see this as being rational is if you donated your miles to charity by booking an award ticket for an aid working or something.
You may have grounds to 'value' the gift at the going cash rate for IRS purposes for the travel booked.
Otherwise, you have a very poor argument. Including your example, being able to sell property for $300,000 and having it appraised for $300,000 are very different things.
Originally Posted by
jackal
FWIW, I disagree with the idea that you can only value a point at what you would be willing to spend in cash. I think it is perfectly rational to value a point at whatever the going rate is, regardless whether you would pay that much for it.
If you buy a $150,000 property that later appraises for $300,000, you don't say, "Well, it's only worth $150,000, because I only would have paid $150,000 for it."