Yes, the pathways are confusing, it isn't helped by the way the paths wrap around the rivers. I've ended up on the wrong side so often...We do have leash law, it isn't followed by everyone, but outside of the core, they tend to be more observant. In the core, particularly on sunny warm days....Lemmings, just lemmings.
Winter riding in Calgary can be done, depends on how far and where. Most routes into the core are fairly well swept, it takes care with clothing, ( that temperature swing mentioned ) and good tires. Last Winter I used Continental Top Contact Winters for most of it, with Ice Spikers for backup on OMG days.