I will translate and adapt here my original answer in Portuguese Resposta de Sergio Diniz para Como é viver na cidade de São Paulo, uma das maiores do mundo?

I lived in São Paulo for twenty nine years and continued to visit it every week, at least until the pandemics...

Living in São Paulo can be heaven or hell, it all depends on individual taste, where you will be living and your lifestyle. Sao Paulo is one of the largest cities in the world, with too many options.

It can be a paradise if:

• You live, work and your children study in the same neighborhood
• If you like arts, theaters and nightclubs (and speak some basic Portuguese to understand it).

• If you live in a neighborhood with good infrastructure and relative safety (surprisingly, Sao Paulo can be safer than some cities in developed countries).

• If your place is flood free
• If you love to eat outside, there are thousands of restaurants, world class level
• If you don't mind living in apartments, condos (and you can afford it ...)

• If professional fulfillment and career is one of the priorities of your life: it is undoubtedly the best center of work in the country.
• If you like excitement, see movement (this phot was taken before pandemics, of course)

• If you live close to the subway (Metro) and can leave your car at home for everyday things.

But It can be hell if:

• You work in one neighborhood, live in another and your children study in yet another place: traffic will drive you crazy, yo.u can spend hours a day in a car. (one of the reasons for me to move)

• If you like peace, barbecue with friends, make food at home, quiet life (like in an American suburd or European small town): it's not quite the style of São Paulo (another reason why I’ve moved)
• If you live in a neighborhood with a lot of crimes and robberies, as in several places on the peripheric side or suburbs (this name have a completely different meaning there), where most of the city's inhabitants live, house iron bars, spikes and electric fences, in addition to guard dogs.

• Whether your home or your daily route is subject to the numerous floods that plague the city during the rainy season. There are people who are even unable to return to their homes during heavy rains or, worse, lose all their belongings in the floodings.

• If you like large houses with backyards, but you can't afford a condominium for security. Burglary and robery can be not so uncommon. (another reason why I moved)
• If you live far away, in poor neighborhoods, don't have subway station nearby and depend on the crowed public bus system.

• If you like good public parks to walk with family and children safely. There are few ones in the city. "But there is Ibirapuera Park!" (the local version of Central Park or Hyde Park). Tell this to anyone who lives in as far as Itaim Paulista, Capao Redondo or Parque Edu Chaves (which only has a park in its name) ...

In summary, Sao Paulo is a city of high contrasts.

ADDITONAL NOTE:

One single image can summarize it all: