When it comes to real estate, I have been lucky, much luckier than a 20-something journalist renting shared spaces with roommates has any right to be.

It began when I arrived as a freshman at the University of Chicago and discovered that my dorm was not the depressing low-rise tower with cinderblock walls and shared bathrooms in the hall that I had braced myself for, something designed by an architect who did dorms when he wasn’t designing prisons. Instead, I was greeted by an historic, if down-at-the-heels, former luxury hotel overlooking Lake Michigan. It had a ballroom, a storied history of mobsters and celebrities, and enormous suites that boasted not only living rooms but also full baths, kitchens and dining rooms. All that was missing was a bellhop.

As first loves often do, the dorm/hotel became the archetype of all that I wanted and expected in a home—beautiful and rambling, abundant in history and friends. It was unreasonable to want it, even more so to expect it, but then, I kept on getting what I wanted. Even more perplexing, it was often through Craiglist. Read More