David Foster Wallace could be the voice of the Millennial Generation despite not being one himself. When Dr. Jeney called him the "consummate complainer", I thought of Facebook and Twitter; after reading "Shipping Out", all I could think was the popular "First World Problems" phrase that often gets thrown around by young people grumbling about WiFi.
Not that I'm complaining, of course. I know older generations see Millennials and like-minded individuals as obnoxious and ungrateful. However, I find that most are very aware of how unimportant what they're complaining about is - but that will not stop them from venting about it. Every person has a right to gripe about whatever they want, even something you wouldn't think they'd have a need to complain about. I think that's exactly the audience David had in mind - knowing that a lot of people find humor and wit in observational humor, especially when coupled with self awareness. If David never acknowledged how silly and bizarre it was to be complaining about anything on a luxury cruise designed for relaxation, his voice as a narrator recounting his experiences would seem as obnoxious as a teenager complaining about their Christmas gifts. But he is careful to spend time, almost in every single passage, to draw attention to the ridiculous standards he quickly adapted to while being pampered - how he realized his slow transition to whiny counter-cultural observer to critical of his afternoon sandwich snack standards. Anyone who has found humor in the "First World Problem" complainers can therefore find humor in this essay thanks to his voice and focus on the intended audience. His self-awareness makes him seem more likeable and fair when judging his fellow passengers, as well.
His organization in the essay breaks the trip into certain episodes, opinions, and observations rather than a retelling of the vacation from start to finish. This allows for an in-depth analysis of every aspect of his trip, all of which serves to support the intended humor. That someone had so much free time on a vacation cruise to investigate and develop a complex opinion about the power of his toilet flush seems bizarre, but still somewhat relatable. Everyone - perhaps without even knowing it - may have also formed loose opinions of strange vacation mates, appliances, waiters, etc. Instead of writing it down and honing in on what they felt, they may have only thought about it in passing, mentioned it to a friend or relative, or shot off a tweet about it. But to see all of these thoughts collected together from one trip would seem absurd and probably surprisingly in-depth. Or maybe that's just me and all the other consummate complainers in the world.