How would this be switched?

[Brakie]

... I would guess that when making a trailing point setout, the fewer cars between the engine and setout, the better? As examples, if the setout was right behind the engine, then we would cut off the rest of the train before the turnout, pull forward and then shove the setout into the turnout. The engineer could easily see what was being done because he is right there at the spur.
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While we would try to keep our train in working order and do exactly what you described but,that wasn't always possible.

Some times the setout may be several cars deep but,no worries we would take all cars between the engine and setout...If the industrial track was to light to handle a heavy locomotive,we would need to use idler cars between the engine and setout or pickup..

Now at the next outlaying yard we would put our train back in working order since we would have the needed room to do the work-unless it was a short train then we simply didn't bother.

Railroading is fairly straight forward and routine as far as the work but,working a local or a urban industrial switch job isn't always as simple as it appears..You may have to drop a setout in front of the car being loaded or unloaded-this makes extra work the next day when you pull that empty car.Then a customer with several spots calls for extra work if you only pulling 1 or 2 loads or empties.You will need to respot the cars that is being loaded or unloaded.