Brendan, thanks for posting this. This was meant to be a fun, provocative article, and I think it succeeded. In my view, most of the courses on this list and the corresponding commentary were completely reasonable. Here's my take on the 5 that I have played on this list (plus one more just to ruffle feathers).
The Country Club is certainly overrated and receives too much love. It is a great course with a lot of fun, interesting features, but you could say that same things about less highly regarded courses in MA like Essex, Myopia, and Eastward Ho! The only reason that TCC is regarded in the world's top 50 courses and these others aren't is its history.
Old Mac probably receives not enough love in general but too much love on this site! I disagree with the author's assessments of the quirky elements of the course. I really enjoy the uniqueness and excitement of Old Mac. Ironically, in creating an homage to an architect who copied holes from other courses and tried to build the same course everywhere
, Doak and Urbina created one of the most unique courses in the world. Nontheless, I still think it's only the third best course at the resort (behind Pacific and Trails), so I guess Old Mac gets too much love or Trails doesn't get enough.
OFCC and Torrey Pines probably deserve their place on this list. If you compare them to all the other courses that recently hosted U.S. Opens, they probably have fewer great holes, more bland (long slog) holes, and less exciting greens. Of course, Golf Magazine's own rankings reflect that, and both courses are probably rated fairly (top 100 in the U.S. but not the world). The "plodding consistency" line about OFCC had me laughing out loud. The exciting/interesting holes like 3, 11, 12, and 14 are outnumbered by the hard but less interesting holes like 1, 2, 7, 8, 9, 10, 17, and 18.
Regarding Olympic, I could not possible disagree more. Olympic is not one of those boring long-slog courses that you might confuse with Medinah or Firestone. There is a ton of quirk, strategy, and fun out there. The routing and use of the hillside is genius. There are so many great holes out there and no weak ones. In my view, Olympic is simply one of the greatest courses in the world. Sure, it's hard to score well relative to par, but par is just a number.
I haven't played Chicago Golf, but I was entertained by the author's comments. I suspect that this course is elevated by its history and exclusiveity not unlike The Country Club. In pictures, the course looks really wide, relatively easy, and not noticeably better than many other Raynor courses which are less highly regarded.