My goodness! What a trip! I use to pull my old trailer with a Mazda Tribute - same vehicle as your Escape. Boy, could I feel the semi's go by!
I, too, found filling the water tank with 5-7 gal. totes to be a real pain. A couple of years ago, I picked up a small hand pump designed for winterizing your RV - looks like a basketball air pump with a hose coming out of the side. Think I bought it at Wall-Mart or Camping World. I've only used it a couple of times, but boy it makes the job a whole lot easier. You might also look into one of those pumps that fit onto the end of your power drill/screwdriver.
2013 Eagle 266RKS
2011 Ford F-150 w/3.5L Ecoboost & H.D. Tow Package