Interesting! Good on you for sharing that.
In my case, I have formed a company which is in the business of providing skilled personnel to the airlines. I train my staff, so I would therefore claim my training costs as tax deductable. Now, I can't answer the questions in part 2, but part 1 should be easy enough to establish, and as for part 3, I would argue that the expenditure does not bring into being an enduring benefit, as the type rating is valueless without a recurrent check.
It also seems to me that it depends where you are paid, and whether or not you are ordinarily resident in NZ. In my case, the last time I undertook contract work, I was paid from a US bank into my Channel Islands bank, and I was not resident in NZ for the required number of days per year. If you treat the training as part of the fulfillment of your contractual obligation, you can probably offset it.
I haven't tried it yet, but may be doing so shortly... I'll let you know.