I know what you mean. Although I have been a voracious reader all my life, particularly history philosophy and geography, I have learned tons in FR these last twelve years, usually through links and references posted by others.
This particular area of your interest is little known by anyone, since ancient history is not all that popular, but your questions are partly addressed in the following book, by our (California) very own Victor Davis Hanson :
Lots of learning there. The Greek civil war which lasted 50 years and was as vicious as our own.
The clearer picture of the cradle(s) of Democracy. A grasp of the cultures in Asia Minor and the Eastern Mediterranean, and more about Greek culture that most people learn in a lifetime.
I have reread this book several times and maps are clear and priceless. Just wish there were more of them.