As with most everything in Ochem it has to do with stability and energy conservation.
What takes more energy- moving around a single puny Hydrogen atom, or moving around a whole Methyl group?
And why is it easier to move a Ph group than a tertiary carbon? Because of resonance the Ph group is stabilized. Yes it is bigger than a tertiary carbon, but since it has resonance it is lower in energy.
Why is it easier to move a tertiary carbon than secondary carbon? Because a tertiary carbon is more stable (lower in energy) than a secondary carbon.
Same reasoning applies to the rest of the question.
With Ochem always ask- What is stable? What is energy efficient?