Echoing the comment about the airport (Congonhas). We nearly bought an apartment in Moema until we realised it was on the flight path, and the noise was very loud.

Also, the flight path can swap - not sure if this is timed or a wind direction related thing.

You can get houses with small gardens in Jardins so as to be near St Pauls.  Whilst many are expensive, the smaller ones are within reach of an ex-pat budget for the larger companies.  With the traffic, if St Paul's is the choice school, and you want a garden, this could be the best bet.  Within striking distance ofIibirapuera too, and avoids airport noise.

I'm not sure how many ex-pats are offered a bullet proof car plus driver!  Probably only really big cheeses.  As for the school, you really want a good international school such as Graded or St Pauls.  There's more 'bilingual' schools than you can shake a stick at, and the quality is similar to bootleg Paraguayan whisky.  A good friend of mine sends his kids to one of these in SP, and 3 years later she can barely say a word in English.

Since the original post was in January, he's probably made his decision long ago without your valuable input (and either has his blindexed car or is kidnapped as you seem to be predicting).

I know plenty of execs/managers/directors/CEOs in various multinational companies, banks, sport clubs, malls etc.