I checked out the Harley Rider Planning tool and it is far, far easier to use than Basecamp. I had tried BC a few times, but found it difficult to use and don't plan on going back to it. The Harley tool is very simple and so far, I've created two routes and loaded them onto my 590 - one local, and the other and early iteration for the 2015 CCR ride.
My Garmin would automatically load Garmin Express when I plugged it in to either the Apple laptop or Windows PC, but could not get Windows to recognize the GPS device (I think it has to do with missing drivers). However, when I used the Apple laptop, it immediately recognized the GPS and I used it to load the two routes.
:bmw: