Two thoughts:

First, from the usage perspective, unless he really wants to use the miles right now, he might want to wait and see if Click is going to have another double mile conversion promotion. It appears that they will have. There was a 10,000 mile limit, but if they keep having them every once in a while, he has the ability to convert 10,000 Click miles at a time into 20,000 miles on his airlines of choice. I know I converted my entire account balance of about 9500 Clicks into about 19,000 airline miles recently, but it was only fortuitous that I had left them in the account and hadn't converted. Actually, leaving them in the account is a good idea anyway, until you know where and when you want to go, and can then decide what airline you need to fly on then put them into.

Second, from the tax perspective, he will get a 1099 from the awarding company listing $2400 as the presumptive value of the prize, and that value will be sent to the IRS as well. However, he can claim something different (lower) on his taxes, but he needs to be ready to substantiate it. So, for example, he needs to get documentable information about how much it costs to buy airline miles that he converts the prize into. Or, if he converts them into tickets, he needs to get information on what he could have purchased the same ticket for on his own, with comparable tickets. As to this second suggestion, this will be hard on him if he converts it into anything above coach, since the full fare value of bus. and first class is outrageous. Therefore, that will probably only work if he converts into coach class tickets.

I have had some experience with this, and have done the legal research. I won a trip to Paris, and declared the value of the trip as what it would have cost me (super-saver tickets) vs. what they valued it as (full-fare coach tickets. Declared a different value on my tax return, IRS computer flagged it a year later and they contacted me, I explained the position and won in the end. However, it certainly was a lot of hassle to save about $300 in taxes in the $1000 difference in valuation I put on the prize than what the prize awarder put on the prize. (Just for information, I think many times those values come from the airlines, etc. who give the seats to a charity, and then take a charitable deduction for an inflated value of the services they donated, but that's just an educated guess.)

For everyone's information, I will come back and repost the name and citation of the case from tax court which said that a taxpayer can declare the value of a prize at the value to him, not the value that it was selling at, or that someone else might have paid, if he can show that he never would have paid that much for such a prize trip (i.e., if you won first class tickets, I think you could legitimately claim the value as a coach class, if you could prove that you never ever pay and fly first class). Will post that shortly.