Crossing culture: Naipaul's short fiction

The third and final set of stories in the Everyman edition of V.S. Naipaul's Collected Short Fiction is from his 1970(?) collection In a Free State: first selection is a prologue about a man taking a boat crossing from Greece to Egypt and with a lot of focus on a "tramp," a rumpled old guy who gets boards the boat and doesn't seem to belong and pretty much bothers everyone else just by his presence. Not clear his connection to anything (in this story collection) or to anyone else, and the mystery is: why does Naipaul's narrator focus so much on this guy? The second selection, which I've just started, is a longer piece about a servant who accompanies his businessman boss on a journey from India to the U.S., where they will settle for sometime; the initial section describes the servant's complete inability to accommodate to conveniences such as a flush toilet on an airplane (he's used to living in a cupboard and socializing with the street people, who sleep on sidewalks). You can see, perhaps, what ties these two pieces together: both focus on an underclass or declasse outsider who cannot fit in with the social and cultural norms around him; both involve a crossing from one continent and culture to another; both focus on the transition between cultures. The outsider/loser status of the central character is fairly typical material for short fiction (less so for novels), but what's particularly striking here is Naipaul's fascination with the outsider: clearly a version of himself, moving from one culture of poverty to a new culture of intellect and gentility, and also from 3rd to 1st world. He made his transitions as a scholarship student and obviously as a gifted and talented young man with great prospects, but there must have always been an element in which he much more identifies with the underling - the tramp, the hobo, the liveried servant. He experiences the transition as one of humiliation and scrutiny.