Dennis Rodkin

A few years back, when investing in residential real estate seemed like a fast money-maker, two guys went in together on three condos at the Metropolis, a terra cotta-clad building at State and Monroe Streets that was being converted from office and retail into 169 condos.

But when the condos were ready for their investors to take possession, the market had changed and the guys couldn’t sell their three units as fast as they had counted on; they ended up in foreclosure. This month, a real-estate agent working for the guys’ lenders sold one of those condos, a two-bedroom unit with parking included that the investors had originally bought for $310,000. The new sale price: $285,000. “That’s hands down a bargain,” says Peter Boland, the @properties agent who sold the condo for...

Last week, months of wrangling in the state legislature over how to fund the metro area’s rail and bus lines resulted in a deal that included an increase on the tax on real-estate transfers in Chicago. That increase¬—$3.50 per $1,000 in value of the property sold—will all go to mass transit, presuming the Chicago City Council approves the tax. (The current tax—$7.50 per $1,000—does not fund mass transit.)

The reasoning behind the measure was that Chicago was paying less than its share for transit because its sales-tax receipts weren’t up to what the collar counties collected. Since the owners of city property—not just housing, but retail and commercial real estate—clearly benefit from...

In the late 1990s, economists, real-estate analysts, and others were puzzled by the housing market. House prices kept going up, confounding everyone’s forecasts. Ten years later, we’re on the other side of that hill: Prices are going down, but nobody seems to know how far they will descend.

Since home prices are a moving target at the moment, up-to-date price data is hard to come by. But I have been hearing routinely that appraisers now use 2004 prices as their benchmarks; just a few months ago, they were using 2005 prices. A 2004 price would mean that after 13 years of increases, we’ve slipped back about three years. That means if you bought your home before 2004, you are still ahead of the game. But that’s only if the market doesn’t fall any farther—and most forecasts say...