It depends no doubt on the underlying visa application, who filed the I-130, I-360 or I-140 on behalf of the applicant, based on what.

If you have a visa in your passport that is not expired you can return. If not, you need one. The extension of status does not extend your visa....

If he is returning to continue on his student visa, he can do so. He will have to file to change status to H1b in order to join the employer.

Your ESTA does not give you any automatic extension of status or change of status to B1/B2. But you could file for such a change of status.

Yes you should be able to change to B1/B2 and remain in lawful status in the U.S. while you sort out your affairs.

Meet with your ICE ERO Officer and request it back with proof of your need to depart the U.S. with tickets etc.

If you arrived in the U.S. and were admitted till July '24, and then filed for an extension, you remain in status until your extension expires....

Usually one gets a social security number together with the work permit. You can file for an ITIN number in the meantime.

Yes, a permanent resident can file an immigrant visa petition for his or her spouse. But the visa will not be available for a long time, perhaps...

That issue seems in my experience only to come up during consular processing. I never recall seeing drug use come up in the U.S. with the medical...