Oz your strategy works ONLY if you are prepared to NOT buy for awhile. I have a client who just did what you are thinking about. They live in Olde Carlsbad and they priced aggressively and sold quickly at below the asking price. They are going to rent but they will not be returning to buy a home until at least 2010-2011. You cannot expect to make the plan you have worthwhile by being able to make a purchase in the short term. To be able to enjoy a rise in equity due to a price reduction, a lower tax base, and a similar lifestyle you will have to be prepared sell now and then simply wait…wait…wait.