In my current play-through I am trying to be more methodical and plan things out to a greater extent than I have previously. One thing I am going to do is use robots I create as Provisioners, so I can name them after the two settlements they link (hoping that they preserve their name and are not renamed "Provisioner")...
To avoid creating too many I was going to create a map of the Settlement links. I found a map online of all the settlements, and they had already marked Provisioner routes to minimize the number of provisioners needed, but the settlements that they chose to connect seemed odd to me in some cases.
So the point of the thread is this: Do Provisioners walk logical straight-line or road-based routes between settlements and if so, wouldn't it make sense to arrange the routes optimally?
That is, connecting Warrick sewage treatment plant to Spectacle island seems a no-brainer since they are very close together... but the map I was studying had Spectacle island continuing the supply chain by going direct to the Castle. True, on the map they are very close as the crow flies, but assuming the provisioner doesn't scuba dive, he'll likely herd the Brahmin along the coast, passing by tons of hostiles in order to get to the Castle.
Jamaica Plain is probably the closest --- by land ---- to the Castle and would save a would-be Spectacle Island-Castle provisioner from walking past Quincy every trip. Unfortunately, to connect Warwick Homestead to the supply chain you pretty much have to come from Jamaica Plain or Murkwater and in either case go through Quincy.
What initially sparked my concern about the routes was the Slog --- whenever I visited there, I'd hear combat in the distance. Turns out, there was a military bot (or two) on the road from the Slog to Greentop Nursery (the closest settlement) and my provisioner would get killed off and I'd lose access to my resources stored at other workshops until a new provisioner took his place. Or, if he is 'essential' until he wakes up and manages to get away from the fight, or until he gets "killed" again and I lose my connection, etc etc.
And if I connected Finch Farm to the Slog, the provisioner would have to walk by the Forged ~every~ trip. So the ~route~ the provisioner walks with his Brahmin can be more or less dangerous depending on which two settlements the provisioner connects.
Rather than use a straight line to connect the nearest settlements ~as the crow flies~ it looks like it would be better to connect settlements that had relatively safe paths between them, even if it meant having one location be a 'hub' from which smaller "legs" branch out. Like, Starlight Drive-In could easily connect to Red Rocket Truck Stop, Abernathy Farm, Sunshine Tidings Co-Op, Greygarden, and Covenant. Five provisioners leaving from Starlight instead of just ONE leaving. But the same ~number~ of provisioners would be needed if you were to try to make one continuous chain, I think.