James,
I think you are absolutely right, Flynn was a foreward thinker and in several ways ahead of his time. Tom considers Flynn a transition architect into the modern age. If he would have lived longer, his influence might have been tremendous. So many of the great architects practicing in America had died before Flynn's death in 1945 at the age of 54. The next generation of American architects practiced their craft in a different direction from their predecessors. Flynn started in 1909, a rudimentary phase, and practiced through the Golden Age up until the day he died in 1945. Architecture was certainly changing over this time period.
By the way, the 9th hole that precedes the tenth depicted above opened as a 614 yard (from the middle of the back tee) uphill 3 shotter that has yet to be reached in 2 shots to this day! I say we should put the tee all the way back and make it 640 yards. Interestingly, the first 400 yards has a severe left to right cant to the fairway which made for a precisely struck fairway wood shot to advance very far up the fairway. Flynn had to squeeze the drawing of RGGC's 9th on the grid paper.
The 8th hole at Rolling Green is a 425 yard par 4 with an island fairway and then a very steep rise to a severely sloped back to front green. The hole plays much more than the scorecard yardage. The 7th is a downhill 488 yard par 5 (4.5 really). Between 8 and 9, it doesn't matter if you score 4,5 or 5,4...if you walk away with 9 strokes between these 2 holes you're in good shape with holes 9 and 10 coming up. I like that the 7th preceeding the next 3 difficult holes plays as sort of a half par. You put pressure on yourself to score well there knowing what is coming up and that is an interesting mindset to play from.