So yeah, the Greybeards are amazingly shallow. No young members. No indication of where new members come from. No history. No interactions with each other. No texts to study. No apparent philosophy, goals, or guiding principles. No chores to do. No goal. No interaction with the society below, other than the people bringing them food for no reason.
To a certain extent I understand why the characters are flat: Voice acting is ruinously expensive and time-consuming. But I don’t understand why the world needs to be this shallow. I’m not asking them to ram a bunch of exposition down our throats. They don’t even need to fill in the details. They just need to hint at the depth and let us extrapolate.
I propose some changes:
If the player asks the Greybeards about politics, the Greybeards answer by explaining that they stay aloof. Long ago Greybeards made a practice of lending their power or knowledge to various leaders, but in the end it did more harm than good. They’re monks, not politicians, and getting involved in power struggles – even for altruistic reasons – dragged them away from their studies and put them in situations where they would misuse the voice.
There. Only a very slight increase in assets, but now there’s enough detail there that we can extrapolate the rest. It’s not perfect. It’s not even interesting yet. But at least it’s not [as] silly.
Really, Skyrim is such an odd entry in this series. It has much less depth and world-building than either of the two previous games. It’s straightforward, simple, and afraid to stray from well-worn cliches. This is a series that brought us the story about mortals using tools to make themselves gods in crazy mushroom land. I can’t help but wonder where that creativity and relish for world-building went. Was it just a couple of people? Did they leave? Was the world made safer and more pedestrian on purpose to make it “more mainstream”?
I’d love to know.
 It’s amazing how many environmental problems you can fix by asking the designer to imagine living there for a day.