Matt, this is very similar to a topic I have been thinking about and actually have a draft post of sitting in my google drive. Is is essentially, what is the value of constraints? To answer your question specifically, many holes in Scotland that play over and around old walls could fall into this category. The Road hole is a great hole that contends with a strict boundary fence.
Below is the thought I have been working through that I think ties into your question in the original post.
Many of the greatest courses had constraints put on them that resulted in creative and great solutions. It is often lamented that if a modern architect built something today like the Road Hole where you hit over a building, it would be their last job. In a recent thread titled “What Killed the Golden Age?”, I (and others) mentioned the rise in technology. Technology essentially eliminated a lot of constraints the Golden Age architects contended with.
In general, this seems like a good thing because it opens up new opportunities that did not previously exist. And every “constrained” option would still be there if the architect wanted. However, it seems like removing constraints leads to less interesting courses, rather than more interesting courses (definitely less varied courses). When constraints are gone, it’s difficult or impossible to see creative and out of the box solutions that may actually be better in the long run.
What if we gave the best modern architects more constraints and watched what they came up with? I don’t suggest we remove all technology from modern design or go back to creating courses with shovels and donkeys. We already operate with relatively firm rules (par 70-72, four or five par 3s, etc.).
It’s cool to see Tom Doak break the mold with Sedge Valley and The Loop, which are radically different. But what if we went further? This could mean a million different things and would vary by site. It would also be arbitrary in the modern age where odd sites would likely be abandoned, but it’s an interesting thought exercise for me.
Could a course with weirder constraints by Coore & Crenshaw be even better than one without? I’m not confident the answer is yes, but it would be interesting to see what new ideas would come to them if they had to contend with the shed on the Road Hole or something equally out of left field.