I don't know the answer to your pump question, but since you already have the tank I would test your mini/trailer combo on your typical terrain that you will need it. A full tank will be quite heavy, a half full tank will change its center of gravity often and may be more difficult to maneuver than a full tank.
I'll also add that it's pretty easy to build a float valve to control your water level in the tank. I made one from a toilet tank float for a swimming pool that often was filled up past full. This would allow you to walk away while your tank fills instead of having to monitor it and not having to deal with overflow.