City I'd Most Like to Live In: second runner-up
#3 City I'd Most Like to Live In: Sao Paulo
This is definitely not a city for everyone. There's no plan, and no real landmarks. There are buildings as far as the eye can see. But I think that may be why I liked it so much. You have to dig a little to love Sao Paulo, but you'll be rewarded by discovering neighborhoods of all different characters from posh to hip, and all sorts of cultural centers like a museum for image and sound.
Food: Not my favorite place to eat. I preferred the simple sandwich and fruit shake cafes to anything else I had in SP.
Art & Design Culture: One of the best in the world. The contemporary art and design scene that can stand on its own without comparisons to Europe or America. There are heaps of exhibits, many of the free.
Public Transport: The metro was great. Very clean, very easy to figure out. I didn't attempt the buses, though I wish I had because there are a lot of places that aren't so accessible by metro (e.g. Ibirapuera Park).
Overall Energy: The whole city is a concrete mass of energy!
Safety: I didn't encounter any problems, but that's because I was already trained in Rio to take tons of precautions, and I didn't venture out of my neighborhood, Jardins, after dark. Supposedly not a very safe city (evidenced by the popularity of armed cars and the prevalence of security guards and tall fences), you should be on your guard all the time. This is probably the one aspect that keeps Sao Paulo from the #2 or even #1 spot for cities I'd most like to live in.
Shopping: SO much fun. There are Brazilian brands that you can't find (easily) in the US, so when someone compliments you on what you're wearing and asks where you got it, you can smile knowingly and say, "Sao Paulo." Plus, all of the stores I went to had a set up where basically the staff who greeted me is also the staff that followed me around and brought me different sizes. But it's not like in the US where if you need a smaller size, they bring you a smaller size. Here, they not only bring you that smaller size, they also bring 5 different styles that you might also like. And when you say, "I like how this pair of jeans is darker," they then bring you 10 more styles. So you could end up leaving the store with something much different than what you came in for. Sort of like the city itself.