The surprising thing to me is that there's no pain for the historical "singular they" (for a generic person, often preceded by "each" or similar words), only for the modern one (for a specific person).
It’s all fun and games till “they” become part of a group and the antecedent is complete guesswork. I use they/them pronouns, but there is a slightly different effort for different usages, and I wish we had something else that was more natural.