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Test it out, or try to get some more local links that will help you rank for the other cities. What I've noticed over the years with Google is that they're pretty good at figuring out the local intent but still serving the same landing page for different cities. Or the opposite way of ranking the local city page for a generic keyword term. With this, you can try to position a few pages to focus on the specific cities and see if it works or if Google is still ranking your main pages. That might save you some headache of having to create dozens of pages but meanwhile could help you see what signals are being picked up.