Krooked, I am in the same boat as you. I need to carry a train load of gear for tending to the ice roads and rental shacks yet I also want to have my portable with so I can scout for a couple hours every day, so a small shack was a must in the plow truck.
This year I went to the Otter Cottage, the smaller Otter one man unit and I love it. It not only fits in my truck with all the gear but I found out I can put in the back of a 1979 Cj5 Jeep! Now that’s portable as the old jeeps are barely big enough for anything let alone a portable. This thing pulls likes a dream, is light enough I can load it by myself with ease and I had it out in high winds during a balmy -12 below and was very comfortable. I also like how roomy it is inside once set up. My old blue one man I would rub the walls with my elbows and this one I can practice kung fu inside without running out of space. jjkrooked you are good sized dude and I can say you will have plenty of room to move in the Otter Cottage.
As far as towing out and hauling gear my shack has these items inside under the travel cover when I hit the ice and it pulls almost effortlessly:
Marcum Flasher
Marcum Camera
Rod bag holding five rods
Tip up tote holding three tips ups and all the pike gear
Tackle box
20lb Propane tank
MR Heater
Battery for rope lights
Camera tripod
Camera
lunch box
five gallon bucket for fish
two gallon bait container
spare gloves/pack
Coffee can full of goodies
Big skimmer
rod holders
Thermos
…and it all packs in nicely under the travel cover without having to stack items other then the rod bags and I simply set the auger carefully on top of the cover in the notch made behind the seat on top of the seat bar. It all works out great and remember I am on Red lake, some very long walks/sled pulls to fishable water and I Jonny P have no complaints. That’s Huge