The first thing to realize about Sao Paulo is that it is utterly enormous. The second is that in comparison to other Brazilian cities, Sao Paulo is pretty much all business. Many Paulistas will tell you that they make their money in Sao Paulo and spend it in Rio (or elsewhere in Brazil). The other thing the Paulistas do is eat well. The restaurants there are superb.

With the exception of the area around the Avenida Paulista, and from there down to the swank shopping on Rua Oscar Friere, Sao Paulo isn't much of a "walking" city. However, if you stay near the Paulista (some of the better hotels are in that neighborhood - - the Intercontinental, L'Hotel, Fasano, Emiliano, Maksoud Plaza, several members of the Melia Group, etc. are in the general neighborhood), you can walk safely and visit MASP (Museo Arte Sao Paulo). Last time I was in town on business several of us arranged a city tour, by taxi, through the hotel concierge; it was inexpensive and well worth the money.

Another thing to consider doing, if you have a full day or two to explore, is to fly to Rio. There are flights practically every 15 minutes, all day long, between the downtown SP airport (Congonhas) and the downtown Rio airport (Santos-Dumont). Get a window seat, because on clear days the approach to Santos-Dumont is spectacular. In Rio it is easy to get to Copacabana, Ipanema and other beaches, to take the funicular to the top of Sugarloaf, or (best of all) to take the cog railway to the famous Statue of Christ the Redeemer atop the Corcovado.

Crime is an issue throughout Brazil, but other than maintaining elevated levels of alertness and avoiding anything that looked risky, I've felt reasonably safe on my walks (and while doing some jogging) in both Sao Paulo and Rio.

There were a few dodgy days in May in SP where there was a big uprising by the local gang (the PCC) against the police. However, these conflicts normally don't affect most of the city like they did during that time and certainly nothing to that degree.

Regarding local transportation, I suggest to go by radio taxi or common taxi (white in SP). Also, the metro (subway) is good during the day especially to avoid SP's massive traffic.

The post about SP not being a walking city is not accurate. You can walk around Jardims, the swank area mentioned, but you can also walk the other way into the historic center and see a lot history during a 2-3 hour stroll. Paulista is good for walking, but not much to see. The area around the Municipal Theatre and the historic center are great for walking and should not be missed.