Just started playing Chicago Express. Fantastic experience so far. However, the one thing I am having an issue wrapping my head around is why one would consistently increase the value of an industrial city. I can think of a couple situations where it would be worthwhile (You have multiple train companies that will benefit you going through the city, for instance).
Situations where you own shares in several companies which are connected to Pittsburgh, for example, are quite common. It's a great use of a turn to boost the value of three of your shares. That said, develop is still most often only used to affect when the round will end.