Expired passport ?

Go ahead and file as soon as possible for your brother. He can get his passport updated now too. But it will be a long time before his priority...

You would have to contact your country's US embassy to get a new passport. If you get married, you may be able to adjust status if you are not...

This is a divorce matter. Category changed to divorce.

Assuming you are her on a B visa you can apply for an extension.

Which category is my work permit renewal should go under?

You should use category c(9) for the work authorization.

Immigration - My father, the petitioner died Jan 2019. How do I prepare for the interview?

You cannot self-sponsor. If your I-130 was approved before his death, then you can find a replacement sponsor for Humanitarian Reinstatement. If...

IMMIGRATION: Let's say an overseas immigrant is rejected due to Public Charge, does the whole process start over?

You will need to address the reason why it was denied. You will need to figure out a way to bolster their finances.

If I'm in a pending asylum stage that means I am undocumented? I entered the country with a B-2 and then applied for asylum,

No, you entered with a valid visa. Undocumented refers to people who enter the US illegally without any inspection or visa.

You should wait for them to reschedule, since they cancelled the original appointment.

You have created a bit of a mess. If you apply for new case, you will need explain what happened the first time. You will need to convince them...