I realize this is too late, but perhaps it might help others who have only a few days in Sao Paulo.
You could hit the center (get off at the Republica stop) and take a walk to see all the street activity, then hop off and get to Consolacao to walk down Rua Augusta into Jardins to get a different stance of the city.
If you're in town over the weekend, the Benedito Calixto antiques fair is a great hangout spot, and it's within walking distance of boho Vila Madalena. I love the weekends in Sao Paulo -- there are always so many cultural activities going on that it's hard to pick which one to do.
Of course, no matter which evening it is, head out. Sao Paulo's nightlife teems with restaurants and clubs, all of which should be experienced.
Enjoy your time in the city!
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