Great post Peter!
While I feel like it would be nice to have 3 or 4 plays at all of the greats, it's just not logistically possible to run the ratings like that. My goal as a rater is to take up as little of everyone's time as possible, thank them for letting me check the place out, and move on. Some guys like to bring a foursome or three family members, etc. to get multiple perspectives, but that to me is counter to my goal of having as light a touch as possible when people are generous. While multiple plays would be nice, I'd rather personally focus on expanding my breadth of knowledge by seeing as much as I can see.
My record of 10x+ courses runs the gamut in quality:
Tedesco, 600+...my home course, combo of homemade/Ross/Stiles/Wogan, etc.
Ralph Myhre @ Middlebury College, 100+...my college home course...homemade!
Va-Jo-WA GC, 55ish...the course closest to our family place in Northern Maine...homemade!
Salem Municipal, 50ish...closest public course to home, an old quirky Stiles 9-holer
Concord CC, 36x...GREAT Ross course, have played a three-round tourney here for about 10 years
Myopia, 35x...worked in the shop there for 14 months, all of 2004
Essex, 30ish...my favorite Ross course, my favorite course in MA
President's, 28x...play the Norfolk Co. Classic here each year...was original Wollaston CC
Taconic, 23x...Williams was Midd's rival in college golf
Neshobe, 20x...closest public course to Middlebury in VT
Salem CC, 16x...Tedesco's sister course and main rival...great Ross course
Indian Ridge CC, 15x...worked at this Phil Wogan course in Summer 2002
Hanover CC, 13x...my wife went to Tuck Business School at Dartmouth
George Wright, 12x...closest public when I lived in Boston
Franklin Park, 10x...see above
Kelley Greens, 10x...exec 9 in Nahant, MA, was once a 3000y Stiles course.
The next tier where I have 7-8-9 rounds would be Bass Rocks (Leeds in Gloucester, MA)/Brae Burn (Ross)/Sand Hills (7), Beverly Golf & Tennis (Stiles), Gannon Municipal (Stiles in Lynn, MA), McGregor Links (Emmet in Saratoga Springs, NY), and The Country Club of Brookline ( 8 ), and Charles River and Granite Links (9).
I would guess my resume is similar to lots of guys who grew up playing private golf in the Boston-area. Lots of Ross, lots of Stiles, and a smattering of local places. Tedesco plays in a local league with Salem/Pine Brook/Weston/Wellesley/Oakley/Charles River/Woodland/Winchester/Brae Burn so these will all be over 10 plays sooner rather than later. All of them are either Ross or Stiles!