At one time, I was in the same camp as Roger: I couldn't get a woodsman neeeeearly as sharp as my 2 blade heads (or 2blades w/bleeders). Then, Charlie spent five minutes showing me what to do with a big file and no kidding, they are THE easiest thing to sharpen out there. Now, I can get them simply wicked sharp with only a 14" file and a small ceramic rod. Check out the tutorial in the how-to section.
As for your choice, I would concur with the others, in part. I think the 2 blade would be the better choice, simply to increase your margin of error. For deer, I don't believe you would have any trouble with penetration with the Woodsman and a 40# bow...if everything goes right. Problem is, in my experience, things going right is the exception rather than the norm.