I have been in this same situation and have done a few things to help make my life a bit better, but do see other improvements that I could implement as I get older (or equipment gets heavier!).
1) I fish out of an Otter Cabin most often by myself and hound, but works ok for two. I keep the bench seat, propane auger, etc. in the sled when loading and pulling out.
2) I put on hyfax right away and works well with ice or limited snow.
3) With more than a bit of snow, I use a "Smitty Sled" that I built and it is crazy how much that helps in moving the sled. From heart attack mode to fairly easy walking.
4) For loading into the truck bed by myself, I use a pair of 2X8 ramps that I cut down to fit into the bed of my 6' truck. I stand in the bed of my truck and the sled pulls up fairly easy on the wooden ramps. Easier than trying to lift when by myself. Improvement here may be an electric winch at some point.
Good luck.