What Organized Challenges or Hunts are There?
None that I know of, but there are several informal challenges in place. For example, you can try to collect 100 stamps from US boxes to join the LbNA 100 Club, or try to collect the stamp of the first box in each state, or collect all the stamp images of a particular clue writer or artist. There also was a group challenge at Letterboxing North America to try to get at least one box in each state by the year 2000. It was close, but no guitar; 47 of 50 states had known letterboxes at the end of 2000. Letterboxing is not supposed to be a competitive sport, so most challenges are between yourself and a good set of clues.