After the global coverage project, all the changes will be made in OSM then CS can be updated at some point.
Check out How to help with missing/broken cities/regions to get background on the current procedure, and check out the CityStrides Roadmap (updated 2020-04-23) post to see what all is being worked on throughout the site.
@JamesChevalier can provide more specific help when he is able.
JP