You could try some bone conducting head phones. I've been wearing the Shokz brand OpenRun headband all day at work for about 5 months now and it's comfy. I use them in bed sometimes but don't fall asleep in them. They have some new wrap around ear ones that might be comfier to sleep in.
Edit: A full charge will last all day and they recharge quickly.
You could check on the new requirements. There are some massive changes this year to the work visa programs. One such change is that you don't have to work in your field of education anymore.