Hi Lee! For what it’s worth, this is a very old (nearly decade-old) thread. OSM’s community and the ecosystem of OSM-powered maps have grown a lot since then, but you wouldn’t know it from looking at these forums, because even the talk-us mailing list is more active. These days, most of the community hangs out on OSMUS Slack. If you’re interested in joining the community there, there are several Kentucky- and Cincinnati-based mappers in the #local-kentucky channel who would be interested in taking a look at your shapefiles and discussing how to properly integrate them into OSM. If not, please feel free to post more information to talk-us.