Do you think an SS examiner is more likely to approve a claim if he/she feels sympathetic?

Yes, it is impossible to negate your feelings if the situation is one where it could go either way. If the situation feels personal you are obviously going to be more inclined to approve it if all the others factors are consistent with an approval. But I also think the reverse is true, if a person has had a bad experience with a person similar to the claimant, if there is any question that the claim is insufficient - they'll be more likely to deny it.