A sidewalk can be a multiuse path. Colloquially the residents of Charleswood wood refer to this section as a sidewalk until the path splits off. I could see the distinction being where the concrete turns to asphalt at the steps, though. I frequent this space on both bike and foot. I would assume you are mapping based on satellite imagery if you do not know this? I will go ahead and revert the feature type to the proper designation. The correct way also conforms with the current feature type of multiuse paths that cross bridges in multiple places in the city such as portage/omands and the maryland bridge.

See the mapping standards below:
osm.wiki/Sidewalks
osm.wiki/How_We_Map

Just because they are part of the bicycle network doesn't mean it is not a sidewalk. At that point the way is parallel to the road, and there is no separation between uses. I can understand the confusion as Winnipegs bike infrastructure is confusing. Are you mapping based on maps or from personal experience?

I use the openstreetmap website and the wiki for best practices

Military is not an approved access= value. Tag access="private" + private="military" is appropriate