Interesting idea. I could perhaps offer it to the hints on the first day. I sort of assumed players would gravitate towards whatever job grabbed their interest and would, in general, have an idea what might happen at each job based on the tropes of the genre.
I think there needs to be a distinction between story and worldbuilding. As an example, if you took a job in the store, you could do really great world building just by having the MC talk to and interact with all the people that live in town. Knowing what they want, what goods they are trying to buy and the problems they are having being stuck in the town would all be great world building. It wouldn't necessarily advance the plot, but it would allow you to sell the weirdness of the setting.
As is, a story where you go to a small town, join the sheriffs and infiltrate a drug gang is way different than one where you become a maid to an eccentric powerful man versus trying to seduce a politician versus being a waitress. (As an aside, I did not expect the waitress job to lead to stripping at the club. My logic being that in the descriptions the job was sold as a way to meet the townsfolk and talk to people. In some ways, I could see the progress from bar>>>strip club but not so much diner>>>strip club.)
If the players are following their jobs throughout the game, that is essentially 4 story paths in one game. I want to use the example of the stats and skills system. You have one scene, but depending on how the player has utilized the rpg elements to create their character, they can interact with the scene and resolve it how they want with their skills. This has choice, replayability, character developlment/roleplaying, and most importantly, doesn't require writing separate scenes for each job.
I think what is driving my concerns is that as a player, so much of the time spent each days feels like it is the job. I basically work, deal with a sleazebag in an alley, and desperately try to explore and unlock side areas before then going on a date. The primary day cycle feels like work then date then sleep. So at this point, from a narrative standpoint, the jobs feel huge. Maybe it is just fear of missing out on my part. Here is my last try at an analogy, in Dragon Age Origins, depending on your Origin, you get a different start to the game and it is a decent chunk of content. It grounds your character, explains their motivations and what makes them unique/special in the world. Then it turns you lose on the plot and you get to take what makes you special and interact with the world and the game. They wrote a game with different character arcs, but not necessarily hugely different grand story arcs. Does this make sense?