>>48078697According to the Shudo novelization, they were hired by Gary's granduncle who had a political position in Pallet Town, basically they are a group of luxury babysitters, as well as a driver to take his grandnephew safely through his trip.
Ignoring the druggedness of some of Shudo's ideas, this seems intelligent to me, the only male child* of a respectable family reaches the age of majority, he wants to see the world, his family allows it, but with certain conditions, it is as if Gary's family knew in advance that he lacked talent for this and only fulfilled his whim to show him the harsh reality and he would return home and fulfill his role with the family business.
It also serves as an excellent analogy to privilege and social differences or simply Shudo wanted to make Ash an underdog from the start.
*Of all the liberties that the anime took, why didn't they include Nanami (Daisy Oak)? Ash having a crush on an older girl and trying uselessly to impress her seemed more credible to me than the ambiguous "I want to be a pokemon master"
His character development would have been to understand the futility of his goal with Daisy and to really learn to enjoy being a pokemon trainer, ending his cycle and leaving room for the next protagonist.