There are islander types and non-island types...
If you're going to live on an island, you probably want to be comfortable with basic handyman type tasks (of course there are plenty of examples of stuff built on islands from people who should never have owned a hammer). It will cost you 2x to get most service performed for you.
If the power/phone/internet goes out, don't expect it to come back in an hour.
Depending on the island location, you really have to live with the weather. If you're on exposed water. There will be times when you're stuck. Getting "off" is usually easier than getting "on" since you'll probably be docking someplace protected. Getting "out to the island" on a really windy day might be impossible.
Getting off and on in the dark can be an adventure too if you're island approach has lots of rocks.
For me the biggest attraction is the privacy. I'll go a whole mid-week without seeing another person May/June/Sept/Oct. I think privacy is very dependent on location though. If you're on the sw side of Rattlesnake you're going to see a lot of boat traffic. If you're on the sw side of Sleeper, you're going to see even more boat traffic + the west alton sandbar craziness.
If you're the type (or the rest of your family is), that needs to get out and do things constantly you're probably not going to be happy on an island.
You might get internet via DSL if you're on the right spot of the right island, but don't expect enough bandwidth for your kids to be constantly be playing online games and watching video. Cell internet works pretty well on many islands these days, but the charges will add up fast.
Try before you buy is probably a great strategy... At least get your real estate agent to take you out there on a nice summer weekend to see how busy things are.
Most places you'll dock your boat on the mainland will have parking and dumpsters. You're likely to be limited in parking though, at least on busy times. It can be a pain shuttling your guests back for forth. Unless you're real close to your mainland the gas costs will add up too.
All in all, I wouldn't trade it for anything..........
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