Love this question Matt. To me, the notion of "getting it" is inextricably linked to the level of interest that a course provides. Almost any course needs to be played repeatedly to really get to know it well. Angles, contours, hazards, green complexes, greens - there is quite a bit to every course. Factor in wind and weather and the number of combinations (or is it permutations? I could never keep that straight) goes way up.
Jason: My view of "getting it" has a lot less to do with how I might play it, or even the "level of interest" (presumably to me) that it provides.
To me, the nature of "getting it" is trying to figure out what the course (meaning, the architect) is attempting to do. Sometimes it's not much; a course not far from where I live was done by a semi-retired guy who had limited space and basically built a bowling alley course for those learning the game to hack around. That's a pretty easy course to "get" after one play.
But by the same token, I don't think it's all that hard to "get" a course like Blue Mound G&CC, a faithfully maintained Raynor here in Wisconsin. Not too taxing off the tee, on land that's pretty unremarkable -- that's a course that's all about the greens and green surrounds. It would surely take me multiple plays to learn exactly how to take on those greens (nearly all of them sizable, thus with great variety of pin positions) from the tee/fairway, and how to tackle putting them (the greens can easily produce 3 and even 4 putts if you are out of position). But it's pretty easy to "get" what that course is trying to do -- it's testing your ability to hit shots into greens in the proper place, and negotiate turbulent green contours.
In contrast, I think Lawsonia is a more difficult course "to get" - there are elements of blindness, width, and deceptiveness that, along with boldly contoured greens in some cases, and penal bunkering, make it a difficult course to fully appreciate its intentions after just one or a few plays. I go there frequently, at least once a year, and I always seem to learn something new with each play. Maybe that's because I'm more "engaged" with it -- I love playing it, so there is an interest in trying to "get" it that is higher than most other courses I play. But I also think it offers a more complicated design than something like Blue Mound.