This particular series of images is closely related to the "Dirt" imagery we talked about above. All the images that detail poverty and a generally miserable existence seem to have to do with service-related jobs: cleaning, delivering, tending to other people's stuff. These are no luxury-wedding planners, and the contrast between working (which the poem frames as a demanding burden) and being royalty (in which you don't have to do anything) is set up by a series of images and plot points that feature poor people serving the rich.
Line 2: Here our first character image is a "plumber with twelve children." Plumbing is not the world's most glamorous job. In fact, it might be the world's least glamorous job, and to cap it all off, the man has to feed 12 kids on a plumber's salary. The fact that he has to win the sweepstakes in order to have any "riches" implies that this particular job sets one up for a miserable life.
Lines 6-9: In this second example of good fortune, the person in question is again in the service industry—this time, working as a housemaid and nanny for a wealthy family. How do we know they're wealthy? Because, by marrying the "oldest son," the nursemaid goes "from diapers to Dior"—which is an image that seems to imply that the luxurious things in life are unattainable if you have a lowly maid's job.
Line 11: This line even has the word "serves" in it. The image here is of a milkman serving rich clients, which implies that he himself is not, in fact, rich. He has to go into real estate—a much more "white collar" job—in order to make his life go from "homogenized" (which can mean both bland and all-the-same), to fancypants "martinis at lunch" by line 16.
Line 30: The first line we get about Cinderella's new stepfamily is this one: "Cinderella was their maid." The implication here is that this is a terribly bad thing—after all, who wants to be relegated to a maid's position after enjoying a life of comparative luxury? (Her father brings back gold and jewels from town, so you know he's got some dough.) Once again, service positions are portrayed as difficult and demanding.
Line 91: This is a strange but kind of neat service-industry-related simile. When the prince gets tired and annoyed after having two mystery-bride-related mishaps with the shoe, he's compared to "a shoe salesman."