Go with what you want to do. I have been trying to fix things for navigational purposes as someone that drives several hundred miles a week. The tagging around here compared to the rest of the state/country is severely lacking structure which I was simply trying to correct.

I changed to match the primary roads based on the city's map in the link I provided. The main purpose in wanting these correct is because I have been mapping out stop signs and it helps to have a "major" and a "minor" road. This makes a tremendous difference when using navigation throughout town.
As far as Medary between 6th and the bypass, that should not be considered a primary path when it has a pedestrian crossing every 100ft. When people use navigation, this sends them down Medary thinking it is a quick path, which it is not, especially during the school day.

Yes. The areas that are marked as living streets are low speed private community roads

From the looks of it, you have a problem with many of my updates although I have stated that updates are due to what I see locally. FYI satellite imagery is very old compared to what actually exists currently

Because that entire building was demolished and rebuilt slightly to the east on the same property. The area that the building used to sit on is now all parking lot and pickup/dropoff lanes.