Brushes: depends on your style
I think how many and what size brushes you should use depends on your style. My style is more realistic than some other people's work and so there are places in my portraits (around eyes and mouth especially) where I use tiny 00 brushes sometimes. But then, on large areas of clothing, especially far away from the face, I use 1 inch wide flats sometimes. Depends on what you are painting and how you like to work.
I find if I grab a brush that is really too big for the area I'm working in that I just can't get the control I need. Then I move a size or two down. I don't think it's always true that a bigger brush is the best one for the job.
That said, if you work with brushes that are smaller than you really need your painting can get an overworked, stiff look pretty fast.
Also, to overcome the habit of painting the whole piece with one brush (something I used to do) I make sure I have tons of clean brushes in all different sizes readily at hand. This also makes it easier for me to use a different brush for each color and each value so I'm not always cleaning them out between colors too. That keeps my colors fresh and prevents my values from all tending towards the mid-tones.
Hope that helps. Good luck!
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