Yeah… My first thought was that he’s probably overthinking it.
Two lines can put a twist in the tree and prematurely break the hinge wood and do exactly the same thing and having it go over sideways because of weak hinge wood. I don’t like pulling trees over to start, but if I do I only ever use one good steel or spectra line.
What I would do, again speaking in generalities, is set one line in the direction of pull, and face it in the direction of pull. I’d put the winch on the biggest deadman I could find, it may be Kevin’s tractor, another tree, building… Whatever. Bouncing on a line if you’re not smooth on the clutch of a tractor or it’s not powerful enough to pull it over can move the tree enough to break the hinge too. A winch is a good, constant tension that can always be backed up with wedges.
Cutting I would open up a nice, big face, probably a little under half, I like the bird’s mouth for pulling because it leaves a lot of travel before closing. I would place my back cut level with the middle of my face and cut it, backed up with wedges, until I had two to four inches or so of hinge, then pull it over.
That’s my take.