I hear you, and I can only speak from my own cultural education, which I learned over time from exposure.

In this meme, I feel that "tipping landlords" is pretty apparent, given that landlords are not employees nor do they provide a service. I've never known anyone to give a tip to a landlord.

"Cuck Chair" should be another tip off as well, since this is a reference to another meme.

You would have to have the cultural-economic knowledge to know

This is likely true of most memes though, where the culture to know, are memes themselves. Darmok and Jalad at Tanagra, and whatnot.

There are indeed already college and university courses to study memes, so if I were to seriously think about what to teach in a highschool I'd probably base the curriculum somewhat on that.