If you find that you're getting hung up on trees and roots along the way, you may want to look into something like this.. I built the cone from 1/4 inch aluminum plate. The choker chain extends through the nose and onto the winch cable and the cone fits over the log butt, so you're always pulling from the tip. Nothing can get between the chain/cable and the log.
I've used it with a snatch block and rope for a while now, this will be the first year using it with a winch. I picked up a Norse (Igland) 290 winch about a week ago.