How does hyperconjugation lead to the directing properties of alkyl group?
Why methyl group is 2,4-directing? This question describes in detail why the methyl group is o,p directing.

However, I think the major point of your misunderstanding is in the interpretation of resonance structures. Resonance structures are not stable structures in their own right.
A set of resonance structures can be used to represent bonding that cannot be represented using classic Lewis structures. The structures do not exist on their own but the true structure can be viewed as an 'average' of all the contributing resonance structures. 

The electrons do not jump between different atoms but are instead delocalized over all of the atoms with a slightly higher chance of being found at the ortho and para positions in the case of toluene and a slightly lower chance of being found at on the methyl carbon. This gives rise to the increased electron density of the ortho and para positions and therefore the increased negative charge and similarly the decreased electron density on the methyl carbon and the positive charge.