Wait for a warm sunny day, after the snow has slid off, and go up there. That way the snow cushions your fall.
The thing to do would probably be to replace the nails with screws. But that would talk along time. A metal roof really shouldn't need caulking, unless you have something on it or through it, and then, caulking is supposed to be secondary, but often is primary.
I learned from a roofer to put the caulking under the metal, so the sun doesn't degrade it, when putting new metal on.
I don't like goin up on a metal roof with a 5 or more pitch.
You can screw a board along the bottom, to rest your feet against, for stability. Maybe bring bucket around
Right Way Roofing contractors based in Utah.
What are you going to tie off to? That is the tough part. Don't tie off to the wifes car, on the other side, unless the keys are in your pocket.