I can only answer the 3rd question. Rob Ford was the king of retail politics. People in his ward loved him because if you called about a pothole he would be t

I can only answer the 3rd question. Rob Ford was the king of retail politics. People in his ward loved him because if you called about a pothole he would be there personally with a work crew the next morning. He became mayor due to the amalgamated Toronto. A previous conservative government combined many outlying cities into Toronto proper, completely changing the makeup of the city. Rob was elected by the suburbs surrounding the old city thanks to promises to keep taxes down and find efficiencies. The core of old Toronto voted overwhelmingly against him. Doug was elected because a tree stump could have beaten the Liberals in the 2018 election. Liberals had been in power for far too long and the province really did need a change. Internal politics and infighting within the PC caucus allowed Doug to extremly narrowly wrest control of leadership. No matter the PC leader was they were going to win the provincial election between a liberal government that did need to go and first past the post voting.