Since you ask, as far as Tilly is concerned, and I would hope that this principle would apply to all architects being discussed, in my mind the most important thing that is needed in order to compile a list of this type is a good understanding of the types of holes and features therein that the architect conisdered as most important.
For example. The most important feature of every hole that Tilly designed, and he this a number of times, is the green entrance. Once a tee and green location was chosen, Tilly considered and designed the entrance to the green before any other feature on that hole. In fact, he once wrote that while examining any course, even if simply there to watch a tournament, he would always stand behind the back of the green and examine how the entrance effected the play of the hole.
So I ask, how often do you study green entrances while playing a Tilly course. If you are to rank his work, this part of it must come first.
Another example, one can't simply choose "par-fives" as a set, and choose his 4 best. Why not? Because Tilly built different types of three-shotters and purposed the play on them quite differently from each other. Let's iullustrate this with the two par-fives on Bethpage Black's front nine, holes 4 & 7.
The 4th hole measured about 490 yards whereas the 7th hole measured 600 yards in 1936 when the course opened. Despite this more than 100 yard difference in length, Tilly considered the 4th to be a true three-shotter while the 7th was designed with the heroic play in mind to possibly reach it in two shots. In fact, the first time it was ever reached in two was in the fall of 1935 when Jimmy Hines was asked to play a round on it to see how it was growing in. He hit driver, three-iron and his second shot went OVER the green! Even with todays super equipment, the hole is still not reachable in two and won't be played that way by almost all at the coming 2009 Open because of the elevation difference between the landing area for the drive and the putting surface. In fact, the green itself, sloping away and downhill from the player convinces even the foolish not to attempt it.
So, for me, understanding of what the design intent for the hole was and seeing how successful it is to having play of that nature happen.
Beauty that inspires is important as well as the simple pleasure of its play that encourages ones desire to go right back to the tee box and play it once again...
These are a few of the qualities I look for when considering ranking holes against each other...