Planning an extended trip, looking for advice.

From BC to the Florida Keys is a weeks travel time pulling a trailer in itself. All driving and no fun. What are your interests and how do you like to occupy your free time when not on the road? Your plans are ambitious IMO. I think you need to pick an area and research what you wish to do there. Go there and relax and explore. Like Canada, the US is a big place and it takes some time to go from one side to the other.