I live in NZ and have done quite a lot of international recruiting of immigrants for positions here. The immigration rules are no problem if, like in most places, you are not too old, reasonably healthy, police checks are ok, etc and have a skill such as a trained tradesman (in the common trades such as electrical, engineering, etc) or are a professional (again in useful things). Like most places, you can also get in if you have a bunch of money to invest.
There is also a Talent (Accredited Employers) Work Policy which regardless of your skill a position offered to you by an employer in this scheme will get you a work permit, as long as your police and health report is ok, and take you to permanent residence in 12 months (assuming that is unchanged from last time I recruited under the policy).
I have lived in both Auckland and Wellington, am a native of neither and have always had the choice of the one I wanted to live in so my choices have been entirely based on preference rather than some kind of allegiance. We live about 60 km north of Wellington on the west coast where the weather is much better (winter daytime lows rarely below 12C and summer highs rarely above 25C) with boat kept in Wellington. The choice between the two is really too personal to comment on.
Despite what has been said, Wellington Harbour is far bigger than Auckland Harbour which is in fact quite small. Auckland does have the Hauraki Gulf outside of it, however, whereas Wellington has Cook Strait so Wellington has much less immediately available sheltered waters. Wellington is also windier, and often compared with Chicago in that (but I have never been to Chicago to make the comparison myself
).
Across Cook Strait (which is only around 12 miles wide at its narrowest but the shortest sailing route is longer at around 28nm or so from Wellington Harbour Heads) are the Marlborough Sounds, together further around Tasman Bay. These are, by far the most extensive sheltered crusing grounds in NZ as a look at a chart or map will show. In the outer parts they can be quite windy and the attractions are more natural than man made. So if one is looking to sail from marina to marina or town to town one will be pretty disappointed. But if ones interests are any of fishing, bird and sea life, natural features, tramping, etc then one will be in ones element. Access to this sailing area is the main reason we live in Wellington and while we have a capable boat small, light boats do the crossing to South Island with no problems by picking their weather and tidal conditions.
We are not into winter sports but both Auckland and Wellington have easy access to sking with many taking off to the mountains for the weekends in winter. It is around a 4 hour drive from either but I guess we don't regard that as far even tho' a small country.
As said by another salaries are not high by many other western country standards (about 30% less than Australia) that being partly offset by cost of living (mainly in lack of hidden outgoings but also in many day to day things). The trick is to get a good paying job so then be reasonably well paid and have the lifestyle. I make this assessment from being a frequent visitor to Australia and less frequent to North America and Europe. I think the house prices have been overstated by another as the median in Auckland is actually approx NZD450,000 and a bit less in Wellington.
All my own family now live in Australia and my wife is not originally a NZ'er so we have no strong family ties here and have considered moving to Australia which has many attractions. Again, it is pretty much the cruising here that has kept us (plus it is green here
) but if into mainly day sailing in a warmer climate then Oz is best - but we like to cruise independantly for weeks at a time. Tasmania is probably the best location there for extensive independant cruising but there again one is out of the hotter weather.
I am not trying to push NZ but just try and provide some information as asked for. There are many great places in the world to live and many we would be happy living in. And, as always, such choices are pretty personal.
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