Does it have a built in seat? Those seats (while nice) weigh a ton. I have an older Kenai that was getting too much (as I'm older myself). I took the seat out, now I have no problem lifting it myself into the pickup. I do empty it and use a 5 gallon bucket in place of the seat.
Now that sled (and the heavy Tundra flip over I bring when with a partner) drag through the snow like trying to drag a Moose uphill. Might be able to be done, but not by me. Build yourself a smitty sled. Hit 2nd hand stores for used cross country skis on the cheap. Search 'smitty sled' on here and make youself one those ski's. Put everything on smitty sled and use two fingers to pull all your gear out. The difference will astound you.