from my obsolete railroad experience and the way i operate my model rr, any move that might require rear end protection gets a caboose. movements that will be protected by a block operator do not require the use of a caboose but they must have the air coupled up if they use the main line.
as for trapping the caboose, you have to figure out your own switching moves but after delivering a train to a connection we used to bring power back across the river from St Louis shoving a cab all the way.
Normally a local would serve more than one customer at a time, so it wouldn’t take just the cars for the farm or just the cars for the oil terminal, etc. It would take cars for serveral industries and switch them then return to the yard or go to the next yard with cars from the several industries.
If the train doesn’t have a caboose its probably a yard engine (assuming you are in an era where trains operated with cabooses.
If the tank terminal wasn’t very far we would leave the caboose or cabin sit since it would be in the way…If it was a shove operation a brakeman would ride the tank car in order to protect the shove and flag crossings.
A simple red flag on the coupler would suffice for end of train protection.All 5 of us would ride in the engine or on one of the end walkway depending direction.
BTW. It was very common for us to do that when traveling short distances…