Dave,
I drew in the route that we took from Skylight to Redfield on your map and attached it. Not sure how to include it in my post like you did. Surprisingly, we came very close to, and crossed through quite a few of your Xs, but yet found that the route was not that bad. Perhaps only the first 0.2 miles were particularly thick with blowdown, but it was smaller blowdown that was easy to negotiate. The route I outlined will save you a little elevation loss and gain as well. Additionally, you might face some marshy terrain heading north of Moss Pond, but I don't know for sure as I have never been that way. You won't loose as much elevation with the route I outlined, but you won't get to see Moss Pond either. This route took us 1 hour, 30 minutes if I remember correctly.
We intentionally did not aim for the summit of Redfield, but to the northeast of the summit so as to intercept the herd path and avoid a lot of the blowdown on the summit ridge. If you are trying to intercept the herd path, it helps to cross it as close to perpendicular as possible. Otherwise, you could be bushwhacking through nasty stuff while the herd path is just 50 feet off to one side or the other.
John