Always go visit your proposed location (be it island or mainland), on a nice Saturday afternoon and get an idea of what the boat traffic is like.
In particular the SW side of Sleeper is an absolute zoo in terms of boat traffic plus the West Alton sandbar is right there.
The channel between Sleeper and Rattlesnake can get pretty busy too. The eastern shore of Sleeper is pretty good... not much boat traffic, some nice long views and protected from NW winds (but of course no sunsets)
The broads side of Rattlesnake is better (lots of boat traffic, but there is a lot of open space).
Barndoor is pretty nice for low boat traffic. The only pinch point is at the very southeast point.
Also don't overlook the number of steps to your cottage from your dock. I find it's an entirely different experience living "on" the water rather than "above" the water.
Finally look up the town's appraised value on the house. At least in Alton they're usually pretty much right on and at least island properties rarely sell for more than their town appraised values.
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