Jeff-
There are a few posts on the information you are requesting here:
This one is the most important one, as it lays out @JamesChevalier’s requested procedure for tracking cahnges when cities are missing (the biggest single workload set when it comes to OSM editing)
It looks like a lot of the info you are talking about is either already in, or would make welcome additions to the OSM Wiki Post.
As for how often OSM edits are going to make their way into CS, this was at the top of the CS Development Roadmap before the surge of new memberships required Strava Sync and Garmin Integration to leapfrog it in priority.
If you search on “overpass” you will get a bunch of discussions James has shared in where he talks about how he brings new OSM data in and filters it. An overpass query is how James processes that and he is constantly making tweaks to it to improve it when things are learned or suggested.
Finally, it is in one of the other posts, but you might really enjoy the Slack channel where discussions can take place about OSM and Citystrides interplay with OSM.