JC Jones,
If your recent visit to The Road was your first and only time playing the course, I'd urge you to take another look; I think you have the course all wrong.
First of all, I don't agree at all that the "bailouts" at TR are generally on the right side; you reference #9, for instance. I think a tee shot down the left side is MUCH safer, calling the right side the bailout side ignores the slope of the fairway and the woods on the right. I'll agree that you can't miss to the right on 10 or 11, but that's hardly the same thing as calling a shot left of that a "bailout".
I think my biggest quarrel with your post, though, is your characterization of 16 as "one of the worst holes in golf". It's one of the most unusual, for sure, and if you can't hit the ball the intended distance and on the intended line, perhaps one of the most difficult, but I find 16 to be thrilling every time I play TR (which is probably in excess of 25 rounds now, fwiw).
And 9 and 16 aren't the only places I disagree with you; the second shot is MUCH more about laying up to a distance you can handle for the third shot rather than which side of the fairway you're on. The right side is only a bailout in the sense that a truly awful shot down the left side is worse, but a good shot down the left side leaves you the same thing as a good shot down the right side. In some other cases, which side is safer from the tee, and which side leaves the shorter approach depends very much on which tees you are playing; 2 is a prime example of this.
But I suppose where I take the most exception to your post is this phrase: "the strategy is largely the same from hole to hole."; nothing could be farther from my experience and feelings about playing The Road. If we assume that the basic strategy on EVERY course is to pick a distance and a line and then execute the shot, more strategy goes into playing TR than any other course I've ever played, or expect to play.
Go back. Play the course again. And again.