Highlander is based on the Camry, not a truck platform
You can probably handle the torque requirements of going up/down steep hills by simply being patient. (Low gear, with a tranny fluid cooler if it gets warm where you are. Alaska, maybe you won't need it.)
But, the unibody construction of the Highlander (frameless) could suffer bending/alignment problems if you load the vehicle heavily *and* drag the TM at the same time. The damage would be progressive: The more often you do this, the more bent-out-of-shape the car-based SUV will get.
You might take note, the new Hybrid Highlander has oodles of torque, available right from ZERO RPMs... but they DIDN'T raise the rated towing capacity. The limiting factor is the body, not the ft-lbs.
I think you should trade it for something truck-based: an "equally beat up" 4-Runner, or Pathfinder, etc. would be more suitable, much less worrisome, much less likely to get damaged by the trips.
Just my opinion, this is really just guessing.
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