Mac,
I look at your appeal as similar to the time when I began seriously collecting live performances of enduring touring bands. I had a nice collection going, with many of the unanimously praised performances in tow; I knew of a few I didn't have; and I wanted to strike out on my own discovering for myself about little-collected performances that most of the collecting community either ignored or had already categorized as not worth their time.
In that vein, I offer these from my Westchester-CT-Long Island area.
MUST SEE (for every reason that architecture is observed and played)
NGLA
Winged Foot East
Yale
Fishers Island
Shinnecock
POSSESS A WEALTH OF ENJOYABLE, EDUCATIONAL FEATURES
Bethpage Black - superb variety of topography from flats to valleys to elevations, the 4th hole (which I think is the finest hole of iits size I've seen), strategic driving angles, heroic paths, broad green design, Tillinghast's routing nod(s) to Pine Valley, general "out and back" quality of the routing brings a serene isolation from other cares and sharpens focus for playing. Though mitigated by the difficulties presented to walking, a round at BB has an excellent sense of adventure like a pine forest hike.
CC of Fairfield - though hodge-podged from 1930s floods and RTJ's subsequent re-routing work, a little-played masterpiece of Raynor imprint. The breathtaking "Sound-side" property is an undeniable advantage, but the courses make the highest and best use of such an awesome locale. Individually there are no indifferent shots, every one holds your focus with some element of danger and opportunity and makes for a proportionally tough four, the more you want to play safely - the longest holes won't reward with fours at all with safe play, unless you have great one-putt fortune. You play to all directions of the compass and traverse all corners of the property, revisiting various sections as you play a subsequent hole. You get semi- camouflaged peeks at upcoming holes and go by interesting perspectives of holes already played. You feel connected to the entire round and the entire course as you play one individual hole and each one individual shot. And after all that wonderfulness... the wind blows. And everything changes; that which was easy becomes nearly impossible, while two and three shot holes can be reached in one fewer.The safe line disappears and becomes the one most fraught with danger while the best play - still fretful - is out over a blindness or near a beach boundary. Little flat bunkers (often no more hazardous than a change of ground surface) that are laughably easy to carry in calm or downwind conditions become Sahara-like sentinels against four when the wind is in the face or quartering. When conditions compound, par means nothing on a single hole or for the course. Please look at the course profile in the Architecture timeline section - it is a well done piece that might give you the added visual zest to track this one down. The only reason I didn't put it in the MUST SEE column is because the property is ridiculously ideal and perfect (architectural history might be greatly different if every architect worked on such a site) and three of the RTJ reworks #1 #11 and #17 are somewhat discordant with the overall experience described; ie - they are a little bland, higher on penal challenge than strategic provocation.
Garden City
Siwanoy
Apawamis
For the purposes of your quest(s) I think all three of these short small former national championship courses will offer a lot of architectural insight into what the best architecture does enduringly...provide amusement and engagement for golfers of different skills, not merely challenge their ability to swing properly. They are completely separate and distinct in their origins and have an architectural lineage (in both design and recent restoration) of three different architectutal camps (Travis & D. Emmet for GCGC, Ross for Siwanoy, Dunn, "Members" & Strong for Apawamis). All three were created and already morphing in the pre-game and first half of the Golden Age. They each have a residue of the quirky, (now-charming) 1892-1901 designs and each mix a disparate amount of ridiculous-looking, sublime and straightforward shot vistas. Even though none of the three were thought "short" in their first 20 years, they are so now, yet each retain their challenge to score via routing that absolutely goes from the green back to the tee. I listed them in about the order I would rank them, but in many ways I would place their "gotta see it" priority in the reverse order. That would put Apawamis first on the list and I'm comfortable saying that - because that little inscrutible beast almost grins at you like a fairy-tale Rumpelstiltskin with its frustrating blinds and pitted vistas. Most of that course feels a 1905 casino/amusement park, but everything is within an average golfer's competence. Siwanoy has fewer visual tricks and arcane hazard, but has the most wickedly sublime slippery contour in its ultra-tiny green complexes while the unchanged routing still defies the worth of mere long-driving. It's also beautifully suburban and is routed expertly across changing topography. I'll leave it to others to more fully describe GCGC as i've only played it once and caddied on it twice, but I can say the coordination is the same: all three courses developed in different ways, on three different properties, by three different architectural inspirations, all retaining the antique feel while satisfying the modern challenges. All three demand an imaginative overall game and general competency in all areas that comprise sound play, especially play from 60 yards and in to the target. They all represent the application of architectural design principles (though many shovels have touched all three) as they were evolving in the first rich period ca. 1898-1919.
Cheers
vk