The trick that finally fixed it was winding the string onto the tuning peg with slack built in on purpose, roughly two to three finger-widths of loose string before the first turn, instead of pulling it taut and winding from there. That slack is what lets the winding wrap downward on the peg instead of stacking on top of itself and needing extra force to tighten.
A string winder tool helps too, but the real fix was the slack technique, since it meant far less cranking by hand at the end when fingers and nails take the most abuse.
It’s a small adjustment, but it turned restringing from a ten-minute wrestling match into something I don’t dread anymore.