On not buying at the wrong time

When we got married in late 2005, we had a notion that maybe we'd buy a condo in Oak Park. That is, until we started looking at condos in Oak Park. Buy an apartment much like the ones I'd been living in for years already, but also pay association fees and property taxes? With little hope for a better parking situation? In an inflated housing market? Sign me up, baby! So we decided that we'd wait until we had the money to buy a house, and not have to sell a condo to do it.

We had a hunch, but are only now fully realizing the financial implications of that decision. We know people who bought condos around that time that still haven't made any money on their investment. It seems like the condo market in the Chicago area is never going recover, and developers are selling unfinished buildings all over the place. In fact, this building across the street from our apartment:



started the condo conversion around late 2005/early 2006, and had an auction of still-unsold units about 6 months ago. Yeah, probably not the best investment.

Fast-forward to early 2008, we realized we were nearing the end of a lease on the third apartment we had lived in during our 2 1/2 years of marriage. We casually went to an open house and the pushy realtor we met there set us up on MLS, started sending us listings and showing us houses. We thought, ok, sure we'll look at some houses. Well, what she showed us were mostly SUPER crappy foreclosures in ugly parts of Berwyn, and started pushing us to make offers on houses we clearly didn't like. This was April 2008, when we all knew there was a lot further to fall before the economy and the housing market really bottomed out, we didn't quite have the cash to get a big enough or nice enough house anyway, and we were pretty happy in our 2-flat apartment with parking & yard. So we decided to renew our lease and revisit the househunting idea in a year...