Thanks so much! I started filling that out - it turns out we still need some addl. info on the property transfer from our local registration office to complete this form. But I wouldn't have known this if you hadn't sent this link, many thanks!
He's concerned that if he border bounces & obtains a NEW visa on arrival, the school will have to totally restart the Ed visa application. That's the hesitation on flying out.
He inadvertently did not obtain the re-entry permit because he didn't realize it was required. He went to visit his 90-year-old father he hasn't seen in 2 years b/c of covid. So it was a mistake. And he doesn't want to fly out now - only his visa is expiring. It's not idle pleasure travel, he just made a mistake.
One tip that may be useful: try booking a flight out with frequent flyer miles if you have any. I recently booked a "just in case" flight out within my visa period using miles, United, & was able to cancel it 100%, miles were put back on my account & the $20 fee was refunded, no fees at all. Check your flyer miles cancelation policy. (You can tell I haven't traveled much during the pandemic. Apparently airlines have loosened up on cancelation policies.)