I told the teacher that they would need to get a new medical back home but the teacher said he is going travelling again and won't have time.
"I'm sorry I can't process your visa as I'm going travelling and won't have time."
That's not going to fly well with employees is it?
It sucks, It's complain worthy but work gets in the way of our plans sometimes. If he wants the job, he has to get the medical. If he doesn't, then the Hong Kong trip is on his own dime.
He seems to have a cavalier attitude towards the process from his end. Fine but it's on him.
You seem to have a lot of stress about all this. I wonder if you are being to nice at times. Shift the stress to him.
With my students, I have one rule for classroom behaviour - Don't make my job more difficult. If you do, I'll make things difficult for you. I don't care how lovely you are generally, don't fuck with my work.
Stop asking and tell him what to do with deadlines. If he can't/won't do it.... Soup Nazi him
No visa for you.