Venture-Lieutenant, Finland—Turku
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Hirelings work by having your character take the time and actions to do what the hireling is doing: Thus you would be using your diplomacy or relevant skills. The only restriction is that you aren't treated as knowing those languages for the purpose of using spells with the linguistic traits, so while you can communicate with people, you can't affect them with spells that require a common language.
For situations where one PC speaks the language but the other doesn't, it feels like it's probably very context sensitive. I don't recall any hard and fast rules for it, but I would probably let the character doing the talking roll for the relevant skill, with the translating character rolling a check to Aid. After all, it's the diplomat that's choosing the phrases and message that's being passed on, and their demeanor and mannerism is probably what the other party is paying attention to.
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Venture-Lieutenant, Finland—Turku
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The translator does know the words. PF doesn't do "conversational/fluent/native speaker", it's just a binary of "either you know the language or you don't."
I could also see a GM stating that the translator makes the roll but the diplomat can roll to aid them, with the translator possibly using follow the expert if they aren't good in diplomacy themselves.
The player who's character is doing the talking should be the one rolling the dice. It doesn't make much sense for one PC to make a moving speech about friendship and unity and collaboration, and then have a separate PC to roll the die, which is part of the reason why I'd make the diplomat roll the main roll and not the translator.
However, situations where one PC happens to speak a language that the target speaks but nodody else does, are very rare. A more common situation could be a "they speak common, but you get +2 bonus to roll if you speak their language" types of situations where you'd run it just like written - others can roll without modifiers, but those that actually speak the language get a bonus. There's dozens of languages in PFS and while you can get a bonus (or even automatic success) in some instances for speaking the correct language, situations where the whole scenario relies on someone actually having the specific correct language are basically nonexistent.
Anyway, it's typically best to err on the side of leniency when the situation is unclear. I mean, a GM could declare that only the players who speak the correct language get to roll for diplomacy (or give others something like, -4 penalty), but if you're in a skill challenge that requires X amount of successes, that would be pretty harsh and would probably lead the group to fail, not because of poor rolls or poor planning, but because of the way the GM decided to interpret the rule, and that's not really a good way to run the game.
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Venture-Lieutenant, Finland—Turku
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I completely missed the last question on your original post:
How does this extend to Hireling Translators? If they’re present presumably they could translate/interpret any of the characters words, so if one player has the boon, the entire party benefits. Is that the intention?
As mentioned before, Hirelings requires your character to take the action and spend the time. If you purchased hireling translator, for you it would work just as if you spoke that language yourself. For others, it wouldn't work as if They spoke the language - it would still work as if YOU spoke it, so we'd be back to "how to run a situation where one PC translates and another speaks."