interesting discussions, all, with a sense of humor :) I understand the big city mentality perfectly, since I was born in New York City.  
Although I haven't been to Sofia, I've been to a number of European cities, and the ones I liked the most were the ancient ones: Rome, Trier, and Vienna. The smaller towns had their charm as well, and I found their history impressive, compared to the United States.
In general, Americans think anything built before the 1700's is old.  
By the way"Vitosha is “the highest” and Iskar is “the deepest"  is part of a humourous Bulgarian folk song. See link, page 94. 
http://www.hopp-zwei-drei.de/Texte/Kurzsicht_Lieder_20101218.pdf