Resonance structures provide a means to show electron delocalization which in turn stabilizes the structure, right? (Yes. - GS). So for simplicity’s sake this means that structures that can be demonstrated using resonance structures for it are more stable than a similar molecule that cant form resonance, right? (Correct. - GS).

^^Could you explain why electron delocalization would be seen as stabilizing if a carbocation or anion would constantly result from this formation? (Electrons will have more space and more opportunities to lower their energy. Same on the math language: there will be more coefficients to optimize in the linear combination of atomic orbitals - GS). Wouldn't a neutral structure with no charged carbons be more stable than one that would observe resonance characteristics?  (The neutral structure will be most contributing. - GS).