Just ran into this particular AI bug today while playing the game.
This AI company started up, and as its first action, built two docks (one by San Diego and another by Los Angeles) and placed a hovercraft at the San Diego dock.
Problem is... while the Los Angeles dock was toward the Pacific Ocean side, the San Diego dock was built in a small lake (geographically it appears it's meant to be the Salton Sea) that's completely disconnected from the Pacific Ocean or any other body of water. So the boat can't actually get from one dock to the other.
How hard could it be for the AI company logic to check that there's a passable, connected water route between the two docks in this maximally simplistic ship route? The game goes as far as to disallow land tool alterations in the water if the modification would impede active boat routes, so clearly it must have some statically-determined notion of the path the boat will take between its stops. But I guess there are some circumstances under which it just does a really poor job of pathfinding. Like, so poor that it believes the ship will take an overland route somehow.
Screenshots and save files below.
Screenshots
Screenshot 1 of 4
Overview of the braindead ship route set up by the AI company.

Screenshot 2 of 4
The AI company doesn't have a low Intelligence score or anything like that. (See game manual page 84 for description of Intelligence attribute.)

Screenshot 3 of 4
Demonstration of water tiles near the San Diego dock where raising the land is disallowed. I raised land on all of the tiles where it was allowed; the one-tile-wide path where there's still water is the area that the game protects because it believes it to be part of the boat's current route.

Screenshot 4 of 4
I also tried messing with the land in front of the Los Angeles dock; it actually allowed me to completely surround the dock with non-water tiles. This would never happen normally. Also, in the earlier screenshots you may have noticed that there's a narrow river a short distance inland that vaguely goes parallel to an imaginary line drawn between San Diego and Los Angeles; I was able to blockade that river with land tiles freely as well wherever I tried, with no complaint from the game.

Save Files
I was making incremental saves with this particular game, so I have one from shortly before the AI company started up, as well as one from after it started up and built its docks in idiotic locations.
Save File 1 of 2: May 11, 1980
North America (West) 1980 13.zip
This is the latest save file I have from before the AI company starts up. I moved the camera over to the San Diego / Los Angeles area and re-saved for testing convenience, but otherwise left it exactly the same.
If you load up this save file, Rottenfish Transport will pop into existence on May ~23; he'll start "Surveying landscape near San Diego" on May ~30; and then he'll start building his ship route on June 1.
Annoyingly, with this save file, while he does build essentially the same ship route, he consistently builds the San Diego dock on the Pacific Ocean side, in exactly the same spot every time (i.e. he doesn't reproduce the buggy behavior where he builds it in the Salton Sea). I suspect this must be due to the scenario random seed being a bit different than it was when I was actually playing (originally, I was building railroad tracks over to the East at the time, which presumably influenced the random seed I guess).
Save File 2 of 2: May 29, 1980
North America (West) 1980 14.zip
This is the save file that I made immediately after the AI company started up and had built its docks, but before it placed the ship down at the San Diego dock. You'll notice the slightly different dock placement compared to the earlier save file, as well as the slightly earlier build date, due to different influences from the game's random system.
With this save file, you can enjoy watching the hovercraft go around and around in circles in the Salton Sea after it departs the San Diego dock; and you can try out some of the land modification stuff that I described earlier for yourself.
Just ran into this particular AI bug today while playing the game.
This AI company started up, and as its first action, built two docks (one by San Diego and another by Los Angeles) and placed a hovercraft at the San Diego dock.
Problem is... while the Los Angeles dock was toward the Pacific Ocean side, the San Diego dock was built in a small lake (geographically it appears it's meant to be the Salton Sea) that's completely disconnected from the Pacific Ocean or any other body of water. So the boat can't actually get from one dock to the other.
How hard could it be for the AI company logic to check that there's a passable, connected water route between the two docks in this maximally simplistic ship route? The game goes as far as to disallow land tool alterations in the water if the modification would impede active boat routes, so clearly it must have some statically-determined notion of the path the boat will take between its stops. But I guess there are some circumstances under which it just does a really poor job of pathfinding. Like, so poor that it believes the ship will take an overland route somehow.
Screenshots and save files below.
Screenshots
Screenshot 1 of 4
Overview of the braindead ship route set up by the AI company.

Screenshot 2 of 4
The AI company doesn't have a low Intelligence score or anything like that. (See game manual page 84 for description of Intelligence attribute.)

Screenshot 3 of 4
Demonstration of water tiles near the San Diego dock where raising the land is disallowed. I raised land on all of the tiles where it was allowed; the one-tile-wide path where there's still water is the area that the game protects because it believes it to be part of the boat's current route.

Screenshot 4 of 4
I also tried messing with the land in front of the Los Angeles dock; it actually allowed me to completely surround the dock with non-water tiles. This would never happen normally. Also, in the earlier screenshots you may have noticed that there's a narrow river a short distance inland that vaguely goes parallel to an imaginary line drawn between San Diego and Los Angeles; I was able to blockade that river with land tiles freely as well wherever I tried, with no complaint from the game.

Save Files
I was making incremental saves with this particular game, so I have one from shortly before the AI company started up, as well as one from after it started up and built its docks in idiotic locations.
Save File 1 of 2: May 11, 1980
North America (West) 1980 13.zip
This is the latest save file I have from before the AI company starts up. I moved the camera over to the San Diego / Los Angeles area and re-saved for testing convenience, but otherwise left it exactly the same.
If you load up this save file, Rottenfish Transport will pop into existence on May ~23; he'll start "Surveying landscape near San Diego" on May ~30; and then he'll start building his ship route on June 1.
Annoyingly, with this save file, while he does build essentially the same ship route, he consistently builds the San Diego dock on the Pacific Ocean side, in exactly the same spot every time (i.e. he doesn't reproduce the buggy behavior where he builds it in the Salton Sea). I suspect this must be due to the scenario random seed being a bit different than it was when I was actually playing (originally, I was building railroad tracks over to the East at the time, which presumably influenced the random seed I guess).
Save File 2 of 2: May 29, 1980
North America (West) 1980 14.zip
This is the save file that I made immediately after the AI company started up and had built its docks, but before it placed the ship down at the San Diego dock. You'll notice the slightly different dock placement compared to the earlier save file, as well as the slightly earlier build date, due to different influences from the game's random system.
With this save file, you can enjoy watching the hovercraft go around and around in circles in the Salton Sea after it departs the San Diego dock; and you can try out some of the land modification stuff that I described earlier for yourself.