I avoid shifting into crossover gears per Shimano. Still getting used to this bike but surprised and pleased with the gear change efficiency. It might be the lighter bike, the 2x10 gearing or the 20 lbs I have dropped but I make less frequent gear changes.
Toronto is a great city. Was there often in the early 70's. ( I was the guy with long hair, big mustache, bell bottoms. )
Stay safe.