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Notes -
You are mostly talking about Big 5 trait agreeableness. There's a good Jordan Peterson lecture about it from before he became politicized. It's convenient for a person's managers, husband (if they're into that), and infants. It's more of a mixed bag for the people possessing it, as you mentioned.
Two highly agreeable people together can be quite annoying. They don't get high quality feedback about each other's preferences, and end up playing guessing games about what the other person wants. They have a bad time raising older children. I can't remember it well enough to find it, but there was a Less Wrong post about how it is actually an onerous imposition to one's host to flaccidly say that whatever they want to do is great, they're totally happy with anything, because this makes more work for the host -- maybe they don't like making a bunch of decisions.
It also encourages people to pursue harmony, intimacy, and compassion, which are real positives. I don’t endorse the “I get whatever I want thing,” but I simply can’t bond with a disagreeable person because I care deeply about fairness and I prefer to resolve conflicts in a way where everyone is heard and cared for. I believe in stating preferences openly, and finding compromise; I’m certainly not interested in docility, but in every kind of human relationship I strongly prefer cooperation and compassion, because we all need it.
I usually think of myself as rather disagreeable, but that does sound like a description an agreeable person would give of themselves. Huh.
Anyway, I would frame the attractiveness of agreeableness as being more about similarity and bonds of affection. I simply don’t like disagreeable people, not because I can’t exploit them (I don’t like exploiting anyone!) but because I feel like I’m constantly being exploited by them, if they even see me as a source of any value, which they usually don’t. I don’t like living like that. I’d rather lay cards on the table and cooperate rather than engage in games of status and one-upmanship.
It’s true that agreeable-agreeable pairings can have their own downsides, but I’ll stack them up against other personality combinations any day, particularly for intimate relationships. Especially if you couple your agreeableness with honesty and forthrightness. Maybe that’s what HEXACO honesty-humility+agreeableness looks like? I don’t know.
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