This TED video is a little long, but mostly funny and interesting. It talks about the design principals of flags and delves into the best and worst city flags in the US.
Afterward, I looked up Madison’s flag and was pretty pleased. It was ranked 11th best in the US: https://en.wikipedia.org/wiki/Flag_of_Madison,_Wisconsin
h/t JT Smith
https://www.youtube.com/watch?v=pnv5iKB2hl4&feature=player_embedded