Hi Shawn,
Greetings from Ontario
One question I saw you posed was filling the fresh water tank. In my experience towing my Bighorn with a full tank it did reduce the pin weight, not by 300 lbs maybe 100 lbs. I tow with SRW and have 3850 CCC with my Landmark loaded for 2 weeks out I am at limit. Stock fuel tank and a 175 lbs of generator in front of the hitch and some times 50 lbs of firewood. Generally I have 1/3 tank of water.
Mountain towing in BC, I plan on that someday I would likely have DRW prior to taking that on. Just my 2 cents worth.
Brian