A lot of people involved in buying and selling names got burnt by buying domains in 2007-08 peak valuations that still to this day cannot be liquidated for the price they were bought for. The interesting thing to me is that most people have a preference to sit on the paper loss until it eventually turns around (they hope) and they will be able to sell without making a loss. I.e selling for under the buying price is taboo for them. I think this is an error that is actually producing more losses for them.
I’ll support my thinking with an example. Say you bought a domain for $100k in 2008. In today’s market the maximum you can get for it is $80k, so you decide to wait. In 2012 you will get to sell the domain for $120k and make 20% on your investment over a course of 4 years. That is a pretty bad ROI. Instead, if you were willing to take a loss and sell the domain in 2009 for $80k, you would initially incur a 20% loss but you could put that $80k you got to work. Say buying and selling more domains, investing in a portfolio etc. From 2009 to 2012 a skilled domain flipper could probably turn that $80k easily into $300k in three years time. So if you would have taked the liquidity route, you could have got a much better ROI on your $100k investment. Pause for thought.