On my first watch of Caddyshack, it's much easier to look at as a series of vignettes as opposed to one cohesive film. There's some spectacularly funny moments in Caddyshack, that perhaps elevate the film far higher than its premise would take it.
Some of the standouts include the synchronized swimming pool segment that was nothing but inspired. Also, Rodney Dangerfield driving his boat through the harbor and how magnificent it was set up. If nothing else, Caddyshack is dream collaboration between many talented comics.