My son rented us a home with a swimming pool in Florida for our forthcoming trip.
You mentioned the difficulty in maintaining speed on cruise with the Harley. I used the one on my Touring for the first real test the other day and, as you suggest, hills are nothing to a Rocket. It held rock solid.
One of our forum members is from BC and a close friend. He has a place in Mesa in which he stays about 5 months out of the year and rides a lot of miles there. One year I kept a bike at his place and visited a few times, riding the Coronado Trail on one visit. Spectacular. I'll send a note to him to check out this thread.