That is a clean little tow rig you got there and i believe the 440 will help but i have had a few big block motorhome's and towed trailers with jeeps and found the hill climbing abilities to be lacking.
I ended up picking a gear for the powerband of the engine and kept it there. Just my thoughts but a Cummings transplant would be the ultimate change up.
P.S. I forgot about the muscle part. It would take a few pounds of hundreds, but it could still work.