buying my house in Kentucky. bought high, sold low, partially due to the market crashing and partly to the house itself
after 5 years of ownership I sold it for 10% less than I bought it for ($20K). In addition to costs to repair and get it ready to sell, plus realtor/closing costs, probably lost $50K on that house (we also caused a flood when we tried to do the upstairs master bath renovation ourselves, which added about $5K to our repair expenses).
buying that house, it came down to that one and a brand new construction which wouldn't have needed any repairs before moving and gained at least some percentage within that 5 years. we chose poorly.