I stayed in the Pestana for 2 nights at the end of June and, following an out-of-town trip, came back for 1 night in the beginning of July. I am a single traveller in my 40's.
For me, there are 3 essential elements which a hotel must have to make my visit enjoyable:
1 comfortable, well-appointed room with powerful shower;
2 good bar/restaurant facilities; and
3 friendly, welcoming staff

The Pestana more than satisfied these criteria and would strongly recommend this hotel for any traveller to Sao Paulo.

I arrived early at the hotel following a long overnight flight and was expecting to be told that I was too early for check-in. Instead the friendly reception staff sorted out an alternative room for me immediately which was a welcome surprise.

I shared a laugh with the porter as he showed me to the room. This is always a great way to make guests feel relaxed; I can't bear the silent elevator journey. I am well aware that this city has a strong "tipping" culture, but I think I can judge whether people are genuine or just out to score a tip. In my judgement, all the staff in the hotel are genuinely friendly and it is nice to show appreciation of that by tipping; with the Pestana staff, I suggest very generously.

One of the highlights for me was the lobby bar. There was soft relaxing guitar music in the corner and the bar staff again proved to be helpful and welcoming. I asked the barman if he could recommend a restaurant and although my Portuguese is not great, we were able to sort this out with little problem.

Overall I was made to feel very welcome and comfortable at the Pestana. I respect the view of life which Paulistanos have which is to enjoy life, have a laugh and make everyone feel at home. I know I'll benefit from a slice of this outlook.