Which game is harder to play at a high skill level, Othello or Checkers? I realize this is a highly subjective question. I have been playing Othello for 35 years or so, and I'm pretty good Othello player at FlyOrDie. I recently tried Checkers which I hadn't played for more than 40 years, and I get wiped out pretty bad. I would guess Othello is conceptually more complicated and Checkers is more about avoiding pitfalls, but I'd like to hear other opinions.
From AI point of view, or at least from a Search-intensive approach, Othello is harder. Checkers has been weakly solved at 2007. Othello has not been solved yet.
From the paper Checkers Is Solved:
Search-intensive approaches to AI will play an increasingly important role in the evolution of the field. With checkers done, the obvious question is whether chess is solvable. Checkers has roughly the square root of the number of positions in chess (somewhere in the 10^40 - 10^50 range). Given the effort required to solve checkers, chess will remain unsolved for a long time, barring the invention of new technology. The disk-flipping game of Othello is the next popular game that is likely to be solved, but it will require considerably more resources than were needed to solve checkers.