If you have been putting off buying a home, don’t delay any longer. Prices and interest rates will both go up this year. Your affordability shrinks.
If you have been putting off selling because prices are so low, this is the year to sell. Put your ideas of a high 2006 price behind you. 50% of sellers in Chicago lose money these days, but your equity stake won’t grow much in next year because home values will go up only a bit, and you stand to make up a lot of the loss on the buy side, because of both low prices and low interest rates.
In both cases, don’t wait for a better market. This is the market and you should just go forward to your next life phase.