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I grew up in the San Juan islands (orcas) so I can try to give you some sort of perspective.
1. Whats the weather really like? It is similar to the rest of the northwest for the most part but can get very very windy in the winter. The power goes out all the time, and that can also effect businesses unless you have a generator.
2. Where do you shop for groceries? On Orcas Island there is a grocery store called Island Market. Its the only real supermarket type grocery store on the island. It is about the size of a QFC. It has everything you need including a deli, but the prices are marked up more than you would find off island. I'm sure that San Juan Island also has a store like this. Lopez and the shaw may not though. There is also a natural foods market where you can find a few things but its very small. There is a convenience type store in each little town on the island. We also would usually take a trip off island and go to costco about once every 2 months and stock up on non perishables, go to target, clothes shopping, etc. because there is NONE of that on the islands.
3. Are there jobs outside of tourist jobs? Not too many. The economy really thrives on tourism, or service jobs like island essentials, the grocery store, convenience store, maids... The few teachers that are needed, the few Doctors, dentists, internet and phone service etc. There are some wildlife type jobs. But I would say the majority of jobs are in tourism and service.
The people-- The people in the San Juans are really their own breed. And there is a funny mix of people there. Not much ethnic diversity at all. You have the bajillionaires and you have the island natives and not a whole lot in between. There is not much of a middle class on the island which makes for a weird demographic. There are a lot of outdoorsy people which is cool. The people also tend to be sort of sheltered. You especially notice this growing up and going to school there.
Speaking of school.... I don't know if thats a factor for you or not. The San Juans are a great place to raise young children, maybe up to the age of about 10-12. Junior High and High School-- not so much. There is very little diversity and the kids tend to be very sheltered to the outside world. The high school is small which is nice in a way but I hated it. It was very hard for me to find friends that I cliqued with. There are some great teachers though, and some not so great ones. The schools are good in terms of academics and the high school is modern. (Orcas Island) Because there is not a lot to do on the island for older kids, some turn to drugs and other stuff out of boredom.
If you've been there before you know that its absolutely beautiful, the air is so clean and fresh, you can see all the stars in the sky.
During the summer tourism months the ferry system can be a huge hassle and you may have to wait several hours to catch a ferry in either direction. Winter is not so bad but watch out for a rocky boat!
There are several places to eat out on the islands with some great food. Obviously, not the same hours or selection you might find off the island though.
I hope this helps. Let me know any other questions you have.
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