That is not actually going on—currently every route is self-contained for choices. Although there are some common elements you might need to play several routes before they’re made explicit, like Bull/Dozer being a thing in basically any route where MC doesn’t pick one of them, or Reggie trying to destroy CrestHaven.
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Personally I'd like a bit more overlap. Currently the only thing that comes to mind is the storm that blows in one day and cancels practise. Having things like the option to go to Howard's book signing, or hearing about Chester visit to the convention, or the get together at the Cafe for the team could be added to every route without too much disruption and might provide a few chances to improve the characters relationships.
Yeah, that’s something that’s a bit lacking IMO—once you pick somebody you’re basically with them 24/7, despite that theoretically all five of the guys are MC’s friends. It’s gotten a bit better with crossovers (Spencer for nostalgia or Dozer/Chester for support or Darius interfering with everybody) than it was earlier on, but is still pretty focused.
Though that can make sense too—I know there are some players who just don’t like one or another of the characters, so having them butt in would be unappreciated.