How is such an intelligent and capable man so often unemployed and almost broke? Yes, he has to raise two children, but he has shown time and time again that he has the qualities to get a high-paying job.
Chapter 191 seems to give a few pieces of information on what happened: Papa Shirogane owned a company, but he was tricked and it was stolen. He then was somehow left with a debt of over 500 million yen... unless he's exaggerating to promote his YouTube channel, which he was able to successfully monetize. However, if the debt really is over 500 million, it will take forever to pay off, considering he "only" gets around 1 million each month, meaning he'll stay perpetually poor.
If Osaragi no longer saw Tsubame as The Faceless back in middle school (Chapter 192), and Chapter 85 is told from her POV, why does Tsubame appear as The Faceless again?
Because her eyes were only on Ishigami at the time.
Why does Osaragi act so cold towards Iino? Yes, she loves Ishigami and supports his relationship with Tsubame, and yes, she has reasons to like Tsubame as well, but she is also fully aware that Iino is suffering. And yet, when Iino tries to talk about it, Osaragi quickly cuts off the conversation.
Precisely. Osaragi has her own feelings towards Ishigami, so it probably hurts to hear Iino talking about the subject. Especially since she's also had to hear Iino complaining about him for the past few years. And it's not like any such conversation would have room for Osaragi's opinion. Every time she's tried to suggest that Iino is incorrect about anything (the 'orgy', Ishigami's character, etc), Iino has refused to listen. Their friendship simply isn't as functional as it appears at first glance- it seems more about Osaragi trying to protect/repay Iino than any personal compatibility. If Osaragi isn't willing to expose her affection to Iino (which, obviously, she hasn't been) all she can really do is break off the conversation. It's hurtful, but it isn't her fault that she's Iino's only friend. Or that she has a life outside of putting up with her antics.
The Shuchi'in elections
Was the school really able to count all the ballots, decide the winner of the student council election and announce the results on the same day as the campaign speeches, before the student council finished cleaning up the gymnasium?