I keep a headlamp in the door pocket of the pickup for after dark trailer checks. It works nice for changing tires or putting on covers.
Check your tow rig for chain fitment. I ride with a guy that has a Yukon and they are not recommended for chains, but he runs his super tight to make them work.
Oregon chain rules: if your trailer has brakes and the chain up sign is up, you have to chain the trailer too. If you are running in a conditional closure condition then you have to chain the trailer whether it has brakes or not. Conditional closures are rare, but you don't want to be stuck somewhere for possibly a couple days until the weather changes.
Small chains, I had a VW back in college so I just cut those chains down to fit my skinny tire chains. Never needed them, but had them in case I legally needed them.
If you put a slush guard on your trailer, or ramps, make sure it will stay in the tilted position by itself to load with one person. Otherwise, you will need to have a weight to put on the rear or a second person. I had an old coil-over shock that I mounted to the top of the tongue under the deck to assist the "tilt" position so I could load up solo.
I also had a piece of bedliner that I cut about 14" x 14" with a 2" hole in the middle. I slid that over my stinger before installing it on the truck. This acted as a flap to keep the Oregon cinders off the tongue jack, latch and ball assembly. Hillbilly I suppose, but worked good to keep that area clean.
Also, check your jack situation. I had a flat on mine one night by myself. I used the jack from the pickup, but it was too tall to fit under the axle once the tire was blown. Anyway, it took some creative cribbing to get the thing changed. After that, I just through in a Hi-Lift so I could lift it from the outer edge and be done. I had put some 1/2" bolts down through the holes in the base and nutted them. This made some spikes so the foot of the jack couldn't be kicked loose on icy roads. The Hi-lift can be intimidating, but I liked the fact that I didn't have to crawl under the trailer to get a jack to work.