It can definitely be done, but you have to be either very good or very lucky to get into the airlines if you are older but with little experience.
I did it by getting all my licences and then heading for Europe, where hiring is done in a far more pragmatic way than it is here. However, you have to get a JAA licence (which means doing all the exams/flight tests again), and you will be treated like a leper on your return to NZ.
If he "won't let it go", then I'd tell him to do it. There is nothing worse in life than looking back and saying "what if...?"
As far as WHERE to do it, I'd advise doing some of it here (if not all of it), however remember that NZ is a bit of a backwater in aviation terms, and he might find some overseas exposure helpful. The Kapiti Aero Club have an established Academy and biggish plans, but can be a bit disorganised (or so I have heard from some students there). The Wellington Aero Club aren't really that well equipped for commercial training, and avoid the Flight Centre at all costs!
He will probably find it better flying at Kapiti anyway, as he will spend a lot less time waiting for his turn to land or take off. When the time comes for busier airspace or instrument approaches, he can just head up to Palmy for that.
If he does go overseas for training, the USA is cheap but the JAA licence is where it's at if he wants to fly in in Europe (unless he has a US citizenship he won't get work in the US). You can do JAA training in the USA (mostly Florida I think), which keeps the cost down.
Hope that helps...