In order to determine the relative stabilities of resonance structures, my textbook gives the following rules (in order):

1. The more covalent bonds a structure has, the more stable it is.

2. Structures in which all of the atoms have a complete valence shell of electrons (i.e., the noble gas structure) are especially stable and make large contributions to the hybrid.

3. Charge separation decreases stability.

4. Resonance contributors with negative charge on highly electronegative atoms are more stable than ones with negative charge on less or non electronegative atoms. Conversely, resonance contributors with positive charge on highly electronegative atoms are less stable than ones with positive charge on non electronegative atoms.

How to determine the relative stability of resonance structures when different rules give contradictory outcomes?

For example, let's consider the following resonance structures:

$$\ce{\overset{+}{C}H2-\underset{1}{O}-CH3}\longleftrightarrow \ce{CH2=\underset{2}{\overset{+}{O}}-CH3}$$

The following are my conclusions with respect to the above rules:

1. Structure 2 is more stable than structure 1 as it has more number of covalent bonds.

2. Structure 2 is more stable than structure 1 as all atoms have noble gas electronic configuration. In structure 1, the leftmost carbon atom has only six valence electrons.

3. There is no charge separation in either of the two structures and so this rule cannot be used to determine the relative stability.

4. Structure 1 is more stable than structure 2 because in the first structure a carbon atom bears a positive charge whereas in the second an oxygen atom carries a positive charge. Since oxygen is more electronegative than carbon or carbon is more electropositive than oxygen, structure 1 is more stable.

Based on conclusions 1 and 2, we could say that structure 2 is more stable. But conclusion 4 contradicts the result given by points 1 and 2. So, how could we determine the relative stability when the outcomes of the rules contradict each other?

Are some rules (out of the given 4) superior over the other? Or do we determine the overall stability by the number of votes on either sides (similar to our community's voting system based on upvotes and downvotes :) ) i.e., structure 2 is more stable since it has two votes (points 1 and 2) supporting it and 1 vote (point 4) against it? If this is the case, what if there are equal number of votes? For example what if points 1 and 2 suggest a structure A is more stable than B whereas points 3 and 4 suggest structure B is more stable than A?

Kindly do not limit your answers to the above two resonating structures. I considered it just to explain the question.

I read the question - How to determine the worst resonance structures out of a given set? and the answers to it. In fact, that question is based on a problem from the same book I follow. But still, I don't understand how to determine the relative stabilities when some rules give contradictory outcomes.

^{Note: I understood resonance structures are hypothetical, i.e., they don't have an existence in the real world. The molecule is best represented by the hybrid of all the structures. As commented in my previous questions on resonance, I've already read the question/answer - What is resonance, and are resonance structures real? and I feel I don't have any misconceptions on the subject.}

In order to determine the relative contributions of resonance structures, my textbook gives the following rules (in order):

1. The more covalent bonds a structure has, the higher it scores.

2. Structures in which all of the atoms have a complete valence shell of electrons (i.e., the noble gas structure) are especially relevant and make large contributions to the hybrid.

3. Charge separation decreases the score.

4. Resonance contributors with negative charge on highly electronegative atoms score higher than ones with negative charge on less or non electronegative atoms. Conversely, resonance contributors with positive charge on highly electronegative atoms score lower than ones with positive charge on non electronegative atoms.

How to determine the relative contribution of resonance structures when different rules give contradictory outcomes?

For example, let's consider the following resonance structures:

$$\ce{\overset{+}{C}H2-\underset{1}{O}-CH3}\longleftrightarrow \ce{CH2=\underset{2}{\overset{+}{O}}-CH3}$$

The following are my conclusions with respect to the above rules:

1. Structure 2 scores higher than structure 1 as it has more number of covalent bonds.

2. Structure 2 scores higher than structure 1 as all atoms have noble gas electronic configuration. In structure 1, the leftmost carbon atom has only six valence electrons.

3. There is no charge separation in either of the two structures and so this rule cannot be used to determine the relative contribution.

4. Structure 1 scores higher than structure 2 because in the first structure a carbon atom bears a positive charge whereas in the second an oxygen atom carries a positive charge. Since oxygen is more electronegative than carbon or carbon is more electropositive than oxygen, structure 1 scores higher.

Based on conclusions 1 and 2, we could say that structure 2 contributes more. But conclusion 4 contradicts the result given by points 1 and 2. So, how could we determine the relative contributions when the outcomes of the rules contradict each other?

Are some rules (out of the given 4) superior over the other? Or do we determine the overall score by the number of votes on either sides (similar to our community's voting system based on upvotes and downvotes :) ) i.e., structure 2 scores higher since it has two votes (points 1 and 2) supporting it and 1 vote (point 4) against it? If this is the case, what if there are equal number of votes? For example what if points 1 and 2 suggest a structure A scores higher than B whereas points 3 and 4 suggest structure B scores higher than A?

Kindly do not limit your answers to the above two resonating structures. I considered it just to explain the question.

I read the question - How to determine the worst resonance structures out of a given set? and the answers to it. In fact, that question is based on a problem from the same book I follow. But still, I don't understand how to determine the relative contributions when some rules give contradictory outcomes.

^{Note: I understood resonance structures are hypothetical, i.e., they don't have an existence in the real world. The molecule is best represented by the hybrid of all the structures. As commented in my previous questions on resonance, I've already read the question/answer - What is resonance, and are resonance structures real? and I feel I don't have any misconceptions on the subject.}