On the general question as posed in the OP, 2023 NEC 230.70(A)(1) says that for a building supplied by a service, "The service disconnecting means shall be installed at a readily accessible location either outside of a building or structure or inside nearest the point of entrance of the service conductors." This phrasing applies the "nearest the point of entrance" requirement only when the disconnecting means is inside.
In contrast, 2023 NEC 225.31(B) says that for a building supplied by a feeder the disconnecting means "shall be installed either inside or outside of the building" and "the disconnecting means shall be at a readily accessible location nearest the point of entrance of the conductors." The "nearest the point of entrance" requirement applies even to an outside disconnect. Apparently you can't put your disconnect on the outside of the building and then run the feeder conductors 100 ft along the outside of the building before they enter the building.
So if you put your service disconnect on a post 3 ft away from the building, does that satisfy 230.70(A)(1)? Seems like it does. Then if you have 2 buildings 6 feet apart, with a single service disconnect on a post that is 3 ft away from each building, does that satisfy 230.70(A)(1) for each building? Seems like it does.
To make the last question interesting, let's assume the feeder conductors run from the single service OCPD to each building run to panels within each building that are far enough inside that they are not "nearest the point of entrance" of the conductors. Either because the feeder conductors are full sized (not a tap), or because using the 25' tap rule we can get far enough into the building.
Cheers, Wayne