One of the worst offenders has to be Newark, NJ and New York, NY. How confusing is it for an international traveler, especially considering how international the area is! On top of that, a major train station in NYC is New York Penn Station, and a major train station in NJ is Newark Penn Station.
Someone can land at Newark Airport, and have to figure out the difference between going to Newark Penn Station or New York Penn Station, which are in opposite directions from the airport.
It makes more sense if you know that there used to be multiple competing private passenger railroads. Penn Station was the station for the Pennsylvania Railroad. The Pennsylvania Railroad had stops in Newark and in New York. Other railroads had their own stations. Some railroads had shared stations, hence Grand Central, and all of the stations called Union Station.
Of course the PRR hasn't existed in 50 years so maybe it's time to change the name...
> between going to Newark Penn Station or New York Penn Station, which are in opposite directions from the airport.
They're in the same direction from the airport, and the train will stop in Newark Penn on the way to New York Penn. Some people will be confused and try to get off in Newark, although the conductors normally try to announce this really clearly.
Someone can land at Newark Airport, and have to figure out the difference between going to Newark Penn Station or New York Penn Station, which are in opposite directions from the airport.