He lives ____ the Isle of Wight.
In America, the "in /on" controversy occrs with Long Island. On tends to be the accertable usage.
That sounds dumb. ^^^ People only say "on" because Island is in the name, as in "He lives on an island", which would be acceptable. But Long Island is a specific place that you can't actually live ON. You wouldn't say "I lived on Pennsylvania until I was five."