Most guys who haul campers regularly have a winch, and a rail down the middle of the trailer, that the wheel on the tongue jack fits into. I've seen regular flatbedders hauling cargo trailers to Canada, but they load with a forklift. Using a rollback wrecker is a good way.
As has been stated already, you need a rail system like what is on a wedge trailer. One of the biggest problems that you are going to encounter with your trailer is if you are pointed down hill when the trailer comes all the way up on your trailer it is going to want to keep rolling until it hits the neck.