Patrick,
I suspect most folks will answer in relation to the courses they would want to see first hand from an architectural standpoint.
I'll answer as a former caddie. Here is what I was concerned with while caddying in high school and college:
How much money are we going to make (you have taken this variable out in this scenario)
How quickly are we going to get around (greens and tees close together, little to no elevation change)
How good are the players we are looping for (caddying is a joy when you are walking down the middle of the fairway with two bags, and simply handing people their putters at the 150 yard mark and not raking many bunkers)
How well are we going to get treated (may be some disagreement here amongst caddies and former caddies, but I only wanted someone to remember my name and treat me with respect through the round)
I'll vote for Pine Tree Golf Club in Boynton Beach, FL and getting Mr. Mucci and guests on a Saturday afternoon in January/February in the late 90's....
Of courses I have played since, I would say the following:
Dallas Country Club (great golfing membership, Texas hospitality, a course squeezed onto a tiny, flat piece of property)
Royal Troon (if I was caddying for members and not the tour bus full of Americans like me...the speed of play slow down enormously)
Westhampton Country Club (flat, lots of Irish last names running around that place...I think I would fit in fine in the caddie ranks out there)
From a pure architectural standpoint, I would say places like Seminole, NGLA, and Cypress in that I would want to see them in various conditions on a day in/day out basis.