Dan, I quit using Ride Planner a few months ago in favor of MyRouteApp.com. I find the route planning to be MUCH easier and they have recently introduced an export option specifically for H-D Itaint system that seems to work well.
I now see too options for importing, Routes and Tracks. The Routes include the specified waypoint (with custom labels), leaving the GPS to determine the routing in between based on the preferences/avoidances entered. The Tracks option imports many data points along the route so as to duplicate the exact routing planned. I've not played with this option much, but on occasion, have lost the custom waypoint labels I had entered.
I have a 10-day ride through LA, KY, WV, VA, TN, NC, and back coming up next week - 5,000 miles in total. The route planning and GPS will be getting a good workout along the way.
Not sure that addresses your specific problem with Ride Planner, but hopefully, gives you some options to consider. Also, a new Itaint update was released today...hopefully some much needed fixes are addressed.