What kind of market would you expect for your house, pinkytoe? Around here, high-end houses, particularly in the outer-ring suburbs, are not selling well at all righ tnow. Under $250K and close to either city? Unless there's a major problem with the house, it's pretty much sold as soon as the for-sale sign in planted in the yard.
So would your house fit into a sells-fast category in your market? If it does, I'd go for it. Particularly if you could handle carrying two houses financially for some months. I think this time is different from 2008. Not hugely different, but enough if you're trading even (or down) and can pay cash and carry the current house for a bit.