Thanks, T.
When I'm about to write the first line of a story, I have a wide array of places from which to start --
What if it was truly a dark and stormy night?
I'm kind of with Ally on this one. By and large, the big name architects of the modern era often get great sites, and can always get out of routing jams with earthwork. TD may be less prone to it, but it's still an option. Thus, I tend to think older architects would be the place to look, probably not the big names. Besides Flynn, it's possible guys like Bill Diddell and Floyd Farley routed a bunch of courses on flat to gently rolling land while moving 50,000 CY of dirt and still coming up with 18 good golf holes (at least in framework, perhaps without bunkers, to be added later, etc.)
I have always generally figured (with exceptions, of course) that the total amount of bulk earthmoving is a pretty good indicator of how natural a routing is. A few times, my mentor had a partially redo a routing because it fit the land so well we didn't have enough cut sources to build greens, tees, etc., and we needed to cut through a few hills. Of course, being trained in the 1950's, it never occurred to them to build more natural, grade level greens to save fill.
(That said, we did spend a lot of time figuring out how to reduce fills. Some architects just waste extra cuts if they have them, others put a note on the plan "Raise this area one foot from plan height to balance cut and fill" or something similar.
I have told the story before, but my jaw has been dropped twice by architects (who shall remain nameless) who simply felt any routing would have a few bad holes and it wasn't worth it to fix them (at least naturally!) Perhaps another judgement factor would be how many iterations they make. While a few routings come quickly (as TD notes with Sebonic) they usually don't and even then, a gca who tries multiple routings first, and then refines the best many times until perfect usually comes up with a pretty good one.