I think a course can be properly evaluated and the subtleties understood in one play, provided that the golfer takes the time to view approaches from both sides of the fairway, and walk around the entire green on every hole. This will usually add a good 10-15 minutes to a round, but for a fair evaluation a necessity. Years ago, Tom Paul came out to Engineers, and drove around spending quite a bit of time walking around every green. We had a great conversation, and drove out to the first green and walked around the left part of the green. There are some wonderful subtle slopes on that side of the green, which really impressed him. By odd chance, that same day, we had a GD rather race around the course in about 1 1/2 hours. Turns out that he sandwiched us between Creek and Piping Rock, and posh clubs got the high marks over the insufficiently studied superior design! Of course I love Creek and PR, and have about 150+ rounds on both, but
Engineers continues to be the Rodney Dangerfield of great courses, and quick evaluations by cart riders has generally been the norm, with more than just the above mentioned race around!