I had a personal stretch from 05-07 when the Deacs went to the Orange Bowl, the Carolina Hurricanes won the Stanley Cup, the Colts won a Super Bowl, the Spurs won an NBA title, and, while their postseasons sucked, the CP3 basketball Deacs were fun and the Braves were in the playoffs. Kind of thought at the time it probably would never get better than that as a sports fan.
There are also probably 10 or less franchises total across all pro and college sports who don't feel like they're owed a championship, so in a way everyone is a little tortured. Of course, as Wake fans we have it the worst because God actually murdered our coach, but whatever.