Wind vs. Wakes
Look at the dock that is already there. The previous owner will have resolved most of the problems you're worried about. This is more about what you want to do: swim from your own dock and beach, water ski from your dock, or just go cruising and anchoring at a sandbar and you don't need a dock, just a mooring.
Most places that need a breakwater will have one already, perhaps with an adjacent portable dock for overflow and guest boats. The breakwater also protects from ice damage, and may provide a protected swimming area for floats, etc regardless of wind and/or wakes.
If you walk around an island and ask each resident, each with a different exposure, each will have reasons why his place is the best one on the island. They'll all be right. If this were not true, there would be a lot more turnover of island properties. And only properties on the south side (where I am) would be desirable.
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