One important thing to know is that what we call "resonance structure" is a byproduct of our chemical notation which can't describe effectively the structure of some compounds using only one chemical structure. Personally I find more appropriate the old term mesomeric structure (meso- Greek mésos in the middle; -merism from Gk. merismos "dividing, partition") because resonance is already used for a phenomena, a real phenomena, in physics that has nothing to do with resonance in chemistry. Furthermore the compound is not continuously changing is structure between the possible resonance structures, like the term resonance seems suggest, but is a "normal steady" compound that simply has an electrons distribution that can not be describe with a single chemical structure.
Why does having equivalent resonating structure give more stability?
The resonance energy is due to the electrons delocalization, so more the electrons are delocalized in the molecule higher is the resonance energy ( this mean a decrease of the overall molecule energy). This is clear in the acetate ion, we can draw a resonance hybrid like this:
Where the electrons are equally distribute (delocalized) between the two oxygen atoms.
However for some compounds the real structure is not always a structure right in the middle between the different resonance structures, the first assumption is true only if the two structures are two equivalent structures, so can occur that electrons are not well delocalized between all the atoms hence the resonance energy is lower and so the overall stability.
In the case of phenolate ion I think the first structure in the figure 2 gives a great contribute to the final structure of the phenolate ion so the electrons are not well delocalized, but if I'm not wrong are mainly in the oxygen atom. Unfortunately I can't find the energy of the different resonance structures.
Finally, however, I think that you should study case by case if the number of the resonance structures or their contributes are determinant to the overall resonance energy taking in account valence and electronegativity of the atoms involved.