Thanks for all the info @rbremer. So I think the next best step would be to get Orphan Cleanup working. I see your task is failing at the DeleteOrphanRemotes step. Is the Actions::Pulp3::OrphanCleanup::DeleteOrphanRepositoryVersions action running to completion for the “Primary” smart proxy (the one likely running on your Katello server)?
If you’re talking about this encryption issue (PulpRpmClient::ApiError HTTP 500 during sync repository - #32 by iballou), then you should be able to run the repair script soon. The latest Pulpcore update got merged into our packaging repo yesterday.