As an update:
August driver is currently broken as August changed their cloud authentication. On the list to review.
Harmony driver should support an unlimited number of remotes. Just add the second hub in AV Family Manager. If you continue to have issues, let us know what's in the Event log for Harmony Driver and myServer.
Homeseer driver update was provided for your specific situation.
Apple is killing iTunes so it's recommended to move off of iTunes Sync driver. Also, the iTunes Sync was developed to connect to a default installation of iTunes on a Windows PC, not on a Mac.