(Sorry this isn't behind a cut; I didn't get that far in my self-taught use of LJ before I left.)
My first impressions of Sao Paulo are that it seems to be a combination of Kuala Lumpur (tropical third-world boomtown, with all the "hey, this doesn't fit...oh well, screw it, build it anyway" city non-planning that entails) and Mexican border town (randomly broken pavement, patches of faux Iberian colonial revival), populated by people who look remarkably like people from the States (a mix of white, black, and Asian).
I did not see Sao Paulo's best face first, either. I took a local bus in from my "airport" hotel. Airport here is in quotes because it's rather far from the airport, actually, in an industrial suburb. I imagine what I saw on the bumpy bus ride to the Metro was akin to flying into JFK, checking into one of the airport hotels on the Belt Parkway, and then riding a bus through Jamaica to the subway.
You could probably not find a worse view of NYC unless you somehow managed to ride from LaGuardia via the South Bronx. And so it was with me and Sao Paulo.
Things improved after I got on the Metro, which is clean, efficient, fast, and only occasionally crowded. It reminded me of Montreal's Metro. Too bad it has to serve a city with five or so times as many people. It really is a good system. I'm sure the place would be totally immobile without it.
The route that the airport shuttle takes is slightly better; it's notable in that Av. Pres. Castelo Branco (which it follows for much of its route) seems to have more churrascarias and cheap (in both senses of the word) motels than any other kind of structure. I hope to try the former but I have brought no one with me to try the latter, which are a really good deal: R$40 ($12) overnight for a room with a whirlpool. I should have done that instead of where I'm staying now but unfortunately they're motels and hard to get to without a car, and no fun without someone to play in the hot tub with.
Speaking of cars, Brazilian drivers have a horrible reputation. I have to say that at least from observation around here, they're no worse than Boston drivers, and possibly not as bad. So far I have seen nothing that would be out of place in Boston. My hotel shuttle driver passed a bus by swinging into the opposing lane and gunning it to get past before the oncoming traffic, but hell, I've seen that done with much less available space on Somerville Ave.
So far there's been nothing like the crazy, random, and stupid things I see on a daily basis driving in Boston. No SUVs, either, probably because gasoline is around $2.50/gal. The pavement is worse here, though, which is saying something.
Also the traffic is so bad that no one can really get up to speed, but then that's also like Boston.
Obligatory food pointer: I haven't actually eaten at a restaurant yet. I've been on the go all day and snacking. I keep coming back to Liberdade, which is historically Sao Paulo Japantown. "Historically" because nowadays many of the shops and restaurants are run by Chinese and Koreans. I spoke Mandarin at one place, for example. (Well, it beats my unintelligible Portuguese.)
If you are stuck in Sao Paulo and have had one too many churrascaria rodizio carnivore blowouts, head over to Liberdade, which even has a Metro stop of the same name, so it's hard to miss. Take the Praca da Liberdade exit from the Metro and walk down either Rua dos Estudantes or even better Rua Galvao Bueno. You can't miss the food, really. Everything from kaiten sushi to a pastry shop like the ones in Japan and Hong Kong. I got salmon o-nigiri from one shop, and assorted pastries from the pastry place (whose contact info I will put in another posting), including moon cake, sesame ball, egg custard tart, and that Brazilian national favorite, the coxinha (deep fried chicken pastry), which I remember and love from the Brazilian places in Allston and Cambridge.
I wouldn't tell you to come down to Sao Paulo to go to Liberdade, but if you somehow find yourself here it's a good place to start.