Yodamom, I think you need to look at it more in terms of percentages than absolute amounts. If the market is down 10% between 2005 & now, then one of the lower priced homes (say $150K in 2005) would be down $15,000, while a $600,000 premier home would be down $60,000.
So you could be "losing" $40K on your sale but buy a house that's now worth $60K less than a while ago. Remember when the market moves up, it's going to move in percentages as well. So a lower price will appreciate slower (same rate but less absolute cash value), a higher priced home faster.
And then, as SNOK says, if you're going to stay, none of this makes a difference anyway. It will eventually be worth more than you paid for it and your heirs can sort it out.
As they used to say, "The time to buy real estate is now!"
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