I would consider for any of these options creating some sort of shoulder harness to pull it with. Wouldn't be too hard, and it would really change the dynamic of how you pull it. I'd rather walk forward uphill with something pulling on my back than have to turn around and pull something by hand(s).
I saw Les Stroud doing that on one of his shows. He was in the snow and pulling a sled (loaded with camera gear).
I still have my ALICE pack. I figure I could carry as much as is comfortable on my back, and use a cart to carry some extra. Small to moderate size obstacles could be overcome by emptying the cart and making multiple trips to get everything up and over.
The added burden involved in bringing all that extra stuff just might be worth it compared to the burden of not having it.
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