I don't think you're doing anything wrong. The ride planner isn't very effective IMHO and the mobile app only exacerbates the problems. Until I got my GPS I'd just use the Map app on my phone along with my music app and plug it into the aux port on my '13 Ultra. It would chew through the phone's battery rather quickly, but it would play music and give voice directions through the head unit. When I plugged the charging cable into the lighter port I would get alternator whine between songs but WTH, If I was lost, I'd deal with the interference until I got to where I was going.
Life is too short to put up with stupidity. Strive every day to educate someone, including yourself!