this may be of some use - info of SYD airport
IMHO I would get his bags sent straight through to AKL
We get ours sent straight through when we fly
Although when we went to Cook Islands, in the summer we said goodbye to our bags in SYD and they went via Auckland to Cook Islands
But my bag was still in Sydney but it arrived during the first night
Take a photo of his bag and give it to him cos they need to know what it looked like to find it easily
Stick a symbol on the side of his bag with duck tape so it is easy for him to identify to get off the belt.
Photocopy his tickets and passport so that he still has his info if it gets lost
I agree with getting a bumbelt and write his flight details on his arm
In SIN imho and ime he will be taken off the plane and put into a holding room --- the womens toilets are very weird
I am sure he will have a deffo brill time
BTW his mobile will work in the airports - cos the signal is sent automatically as it roams