My realtor rolled her eyes and declared it a "dumpito"—a little dump—and was so appalled when I announced I was going to buy the place that she didn't speak to me for a year. The 70-year-old house at the end of a short dead-end lane in Santa Fe, New Mexico's Historic District amounted to 800-square-feet of crumbling adobe, inoperable double-hung windows, and a ceiling so low I had to duck to walk across one of the rooms.

An email exchange with Mountain contributors on assignment.