not really new/a regular here but I played it a while ago and in my opinion you have to be the kind of guy that finds everything that doesn't make sense funny. some of the things I find the funniest are sort of subtle, like all the semi-obscure game rips. the background of the dating sim part is from a nancy drew game which I played like 15 years ago, that made me flip out. the whole dating sim part is great too and somehow I think without the girl's dumb look it wouldn't be as funny. "may be erotic for child" was great too
some things I found the funniest: the shrekmono (imagine if the meme didn't exist), incan gold, columbus day transformation, all of truckpump, vinceborg writing the furry poem, barkley/other character's weird outbursts (so desu ne, gatdam, baka, etc), gun's, the obvious plotholes, out of place sprites, and many more
I think thecatamites' Goblet Grotto kind of has this sense of humor but to a more insane degree, and some of million dollar extreme's stuff (example paradigm shift)