One of the most interesting aspects of Rolling Green is that much like Donald Ross, Flynn was amazingly adept at finding the high spots to locate tees and greens, and probably even more inspired at routing.
As with many of his northeast courses, the property has very significant elevation change, yet at no point does one feel the physical effect nor are any areas on the site wasted because Flynn was not able to creatively utilize them. At Rolling Green, he attacks some of the uphills and downhills head on, such as the gradually climbing 9th or the vistas from the 7th and 11th tees, while in other places he moves to these elevation changes rather diagonally, utilzing the existing sideslopes to great advantage, such as the par three 10th and 14th holes, or the approach to 2, 7, and 18. Flynn transitions one across the property so adeptly that you look back and realize you've made significant climbs or ascents with the previous shot without sometimes being aware of their impact on your shot, and there is a great deal of visual deception inherent in that approach.
All in all, I would heartily concur with previous comments that cited the great variety of holes that Flynn was able to find on the property, as well as the subsequent balance and pacing. Although there are quite a number of really demanding and difficult holes, at no point does the golfer feel beaten down, or that the challenge is insurmountable...only inspiring.
The greens are as good as I've seen from Flynn, with all sort of countering contours running in opposition to the fall of the land, and almost every green can play from relatively easy to exceedingly stringent depending on hole location. The bunkering is thoughtful, and at greenside can really influence what might be attainable. There are plenty of holes where finding the middle of the green is often the best play, rather than firing at tucked pins.
I would also concur that a number of trees planted in the past thirty years should be removed, and many of them are cited in the club's Master Plan. However, there are also many beautiful mature trees, well back from the playing avenues, that add a certain majesty and grace to the property and it's clear from everything I've seen that Flynn wanted them them for hole isolation.
Unusually, the course ends with a pair of shortish par fives at 485 and 505, for a par of 71 and a total course yardage of 6628 yards. Flynn had an affinity for "half par" holes, and there is evidence that those holes fall into that category. There is some discussion at present to shorten 18 and make it a long par four finish, but in my opinion, 17 would be the better of the two as a bear of a par four at slightly reduced yardage (or perhaps even the same from the back tee) with a gambling tee shot needed to have a shot at the green. Leaving 18 to follow as a real potential birdie hole would seem to me to be more consistent with the variety, balance, and sense of optimism that are the hallmarks of this wonderful course.