Starting from the beginning is the absolute best, in my opinion. The original series is so much fun, and as much as I love TNG and others, I know that nothing will come close to the cultural impact that the original had. It was prime time, mainstream, and riding the energy that the country had for space in the 1960s, with a message of hope and cooperation. That being said, prepare for a decent mix of goofiness too, lol.
They're still cities, but people tend to start calling them "rural" when you get a certain distance from the big cities and things spread out, often also near farmland and/or nature.
Yours is troubling