I have to be careful when I discuss Tobacco Road, simply because I love the golf course so much. In the genetic lottery, I somehow got two loyalty genes, and that often comes into play when I talk about golf courses that I love.
Many years ago, Tom Huckaby explained to me that the larger-than-normal gap between the course rating and the slope rating of TR was one of the factors that kept the course from being rated higher, and I get that; I really do. There are particular shots that a high handicapper just simply won't be able to hit; the second shot into #9 of course comes to mind. I also agree 100% that a low index who is having a good day and is disciplined can typically post a good score at ANY Strantz course, including The Road, because the targets are so generous, especially off the tee, assuming that the player is playing appropriate tees.
And so I understand the contention by some that TR is "easy", but I don't find that argument to be wholly consistent, given that it is based on the idea of a good player playing well and hitting intended targets, which is a good recipe for low scores at ANY course. Whether or not scores at TR are low more often than at other challenging courses isn't provable, and if the course rating folks from the CGA have done their jobs well, probably shouldn't be true anyway.
But as to ANY possibility of being "boring", that's a point about The Road I don't think I could ever grasp, much less concede. I don't care how many times you've played the course, the first tee shot will stir interest. As will the second shot on #1, and so on around the course. The third shot on #13 is just a cool shot, whether you've hit it once or a thousand times. The size and shape of the green on #9 had better hold your interest in proper club selection, even if you are a scratch golfer who is having a good day. The tee shot on #8 is really easy, but depending on the pin position, the second shot is challenging for anybody; end up on the lower level with a back right pin, and you'll do well to three putt. And so on around the course. Pulling the right clubs and executing the right shots on #16 is thrilling to me, even when I play the hole poorly.
The Road is the only place I have EVER played where, with a yardage book, a phone app, and a laser I still don't know exactly what club to hit, even on days when I am playing well, and I find that to be completely exhilarating. The idea that players, even very good ones, should play it once and then stay away is one to which I can't connect, and is NOT my experience with the people I've been around; most can't get enough of it.