Tyll,
Don't forget to adjust for inflation.
Using the CPI Inflation Calculator at http://www.bls.gov/data/inflation_calculator.htm
$249 year 2000 dollars are worth $326.39 2011 dollars (for now ;) )
But more likely, the marketing departments have discovered the power of "Price Anchoring"
( http://youarenotsosmart.com/2010/07/27/anchoring-effect/ )
If your only headphone is $250, that might be considered expensive
(considering, say, how many Big Mac's you could get instead)
But if you compare it to, say, a $1000 headphone, it seems like a relative bargain. Why, you've just saved $750!
Plus, who pays retail anyway :)