This thing has been oddly frustrating. I've mostly been playing around with the United States quiz (because it frustrates me to know that I don't know where Brattleboro is), but am still working up the courage to give the "Flag" and "Photos of the World" challenge another try. It's one thing to realize that I don't understand where things are in Vermont (which I'm giving myself a pass on as it was one of the two states that was left out of my New England Roadtrip a while back) but I'm not sure I can still consider myself to be aware of international politics if I cannot recall from memory either the flag of Eritrea or what monuments in Warsaw look like, and I'm not sure my self esteem could take that hit.
Also, if someone can tell me what the Roller City is, I'd love to know. They always ask it during the "City Nicknames" round, I always promptly forget where it is and Google keeps directing me to roller derby things, which, while awesome, are not what I'm looking for.