OK I have to say all of these responses are HILARIOUS and some are true and others not even close, lol. SO the island is not large 14X5 or so, in miles, in the winter it'll take you 45 minutes from end to end give or take, in the summer about 2 hours (yeah seriously). There are plenty of jobs on the island and it just depends on what your wife wants/can do. The boats run YEAR ROUND, the slow boat year round, the fast boat for the Steamship Authority runs part time like April-January, something like that. The Hyline only has fast boats and they run year round. Its expensive to live on the island but the pay for the local jobs makes people stay, no really. My wife was a secretary/office manager for the construction company she worked for (she was the only office employee) she made $27 an hour and was only part time. This was after 6 years, she started at $21 an hour, so yes things are expensive but the pay is also their. It is an INCREDIBLE island that you may love or hate, you have to go their thinking "it is what it is" if you have an open mind about it you will love it. The island has around 12,000-15,000 residents year round and it grows to an estimated 60,000-70,000 in the summer months. I still have plenty of friends who live there and will never leave.
You can't live off island and commute, you have to live on island, whether it be fog or wind you'll either have no boats or no planes or neither and you are stuck on/off island. Housing is one of the hardest things to get and keep on island, there is a TON of seasonal rentals but summer is big money. It is a true island for the MEGA rich, the millionaires and billionaires are PLENTY in the summer time, stupid money is kind of how its said, lol. As an example for the stupid money we had a GLF5 land and then the owner took his private helicopter from the airport to his yacht parked out in the harbor (they could've driven and taken their tender boat) but decided to "make a statement", lol. Another was we had a GLF4 land from Aspen I believe and the only "people" on it were the owners dogs who were dropped off, yes that really happened, go get the dogs and bring them to us on ACK. Now as for working jobs, a teacher friend of mine , who made $75,000 a year to start, worked as a waitress in the summer time and worked doubles and such all summer and made $30,000 in tips, she paid for her new truck essentially in cash.
Sorry this is so long but there's really a lot about the island good and bad, now some of the bad, we set the record for most days with out seeing the sun, 41 days if i remember correctly, straight grey overcast for 41 days straight. The wind blows and blows, 20-30 mph is "kind of normal" The island is literally called the Grey Lady for all the fog the island gets, whats crazy is you can be 600-1,000 RVR at the airport and it will be sunny and not a "cloud in the sky in town", which is 3 miles away. The weather is some of the most fascinating thing I have seen their. Majority of the islands restaurants and hotels shut down for the winter time, about 75-85% close and then reopen for spring, summer and fall. Getting on and off the island is not that hard, yes it has its moments and can certainly be a pain in the ass but its not terrible. The boats and planes all offer islander discounts year round which helps.
I bought my house after the market tanked (2010), but you see about Nantucket is that the island was affected by the crash a year or so after everyone and rebound before everyone. There is a TON of building going on on island so prices are all over the place, yes it is pretty expensive not gonna lie to you there but its possible to buy. Another things was that a few of the controllers, me included, had 2nd jobs waiting tables or doing whatever to A. help but B. b/c the pay is worth it. Well that's all for now and I can certainly fill you in more if you really want, the facility is AMAZING and I loved working their everyday, I transferred to DAB to get my radar ticket and I went to Riddle here in Daytona and my wife went to college in Jacksonville.