I have this conversation with friends pretty regularly. I would rather play one great course five times in a row instead of play five different courses, because I like to "get to know" a course. This seems to be a pretty minority view for my friends, who are trying to play all the best courses they can, and would much rather play five different great courses.
I think there is a difference in a visitor's experience, a resort experience, and a member's experience. I just want to know if you all see a difference between these, and if so, what attributes do you want in each type of course experience?
Not accounting for reality (cost and ability) if given the option to play NGLA, Shinnecock, Sebonack, Friarshead and Maidstone vs five rounds on one of them I'm picking the five different courses vs one 5x. I totally agree that playing one course multiple times is likely a better experience, but the reality is I've never played, and probably never will play a single one of those courses so the chance to play 5 is something I don't think I could pass up. When going to the UK/Ireland my trips now include playing one course a number of times with just a few other one offs, but that's because I've made the trips circling the islands playing a new course or two every day.
To answer the question since I have limited time, resources and connections the factors I utilize to decide where I'm playing are who with, proximity, value, quality, pace of play and does it provide the ability to detach from the daily grind.
When playing with a friend I rarely see the course doesn't matter very much (I don't have friends who would be willing to pay $500+ for a round of golf).
For a home course I need to be able to play early on the weekends, walk at a reasonable pace and it needs to provide a setting that I can detach from the daily grind. Other things that matter are proximity to home, quality and value.
For an away course quality and value are the things that I use to make my decision on where to play.
Admittedly quality is a hard thing to assess before visiting and value is hard thing to quantify.