I've lived in all four quadrants and my fundamental rule of choosing a Calgary neighborhood is live on the same side of the river that you work. There are only so many crossings and they are all choke points.
Also, if you can - live east of work so you aren't driving into the sun.
Given that Kensington and Highfield are on opposite sides, I recommend OP look into a new wife.
More constructively, we looked hard at Lakeview and I still think it's great but kinda overrun with NIMBYs. Getting better access out the west side is a big improvement since 37th was upgraded.
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