[orulz]

I would say that the riveted steel structure of the L is iconic, historic, and objectively cool in much the same way as the Eiffel tower. Said hypothetical student from Singapore, doesn't expect or want Chicago to look like Singapore.

It is good for CTA to prioritize structural integrity if funding for maintenance is limited, but if they had resources to pay more attention to aesthetics, it would make a big difference in the overall impression of the system. The sections that are painted light colors really do just look grungy. With a bit more attention to upkeep and cleanliness of structures and stations, the L could maintain its distinctive character while simultaneously being a world-class transit system.