See, I had no problem with the mayor/island story. To me, at least, it made sense. Merlyn beat Oliver. Straight up proved he was better than him. (Almost as if, Oliver had a "downfall".) Oliver then began training to make himself not only a better Green Arrow, but a better Oliver Queen. He was able to optimize all of his strengths to bring about the maximum amount of utility. Probably at his peak to be honest. It made him believe that he was finally good enough for Black Canary. Frankly, Ollie should have retired at that point. Roy took over his duties in the league and Conner could cover Star City w/ Mia. But hey, if they had done that, we would have never gotten the Robinson masterpiece and the upcoming giant leap backwards "Rise of Arsenal."