A recent piece I read in USA Today indicating, on average across airlines, the redemption value of frequent flier miles has dropped from 2 cents a mile to 1.2 cents a mile. Reasons included the number of miles being earned through credit cards and bonus mile opportunities in the weak travel economy.
So paying twice that amount to buy miles only makes sense if you can get just that same value out when redeeming them, which is possible depending on the route and the award.
I wasn't aware that the miles offered at ticket purchase were discounted; I guess I just skip through that screen very fast.