Hi Raymond, I am physically and metaphysically too far away from Chicago to even attempt at advice on piloting such a move. I know my limitation:0)
None-the-less, I would imagine watching the share price of housing related stocks, and for headlines reading thus, "Housing is Dead" would be apart of the navigation program.
You also need to consider the unnecessarily complicated, inadvisably convoluted, sometimes totally incomprehensible, and high maintenance US tax system concerning how long the main residence can be sold without having bought another main residence, and still qualify for the gains tax exclusion, the likely range of home price drop, etc, etc.
For owner-resident, I would (did) buy when I thought I was happy with the price. I bought my first place in Hong Kong in December of 1998 (closing in Feb 1999) at the depth of our 60% 'downward technical adjustment phase', when pricing went from USD 2,200 to USD 900 per square foot. I was happy to rent for 11 years (bachelor, of course, else wife would have revolted) as price rose steadily up but rent much less so. Got married in 97, but promptly sent wife on her way to B-school, thus avoided buying residence at peak, in exchange for an 4-SUV tuition bill and some free time :0)
Speculation on the main residence is to be avoided if possible, because we can be wrong, inflation zips up, housing price responds promptly, and wife screams every night while living in a rented house.
Chugs, Jay
P.S. We are in uncharted territory, and we do not have the imagination to guarantee a smooth and successful navigation.
The US innovation of mortgage backed securities has more closely and fatefully linked US residential housing to the global financial market, thus anything can happen.
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