Depending on which marina you wish to overwinter in, your going to have to deal with the lake freezing over. Sometimes it freezes over later than other years, but it will freeze. A bubbler dockside is a start, but be prepared to deal with the ice. Otherwise, there are several nice marinas downtown or in the suburbs, depending if you wanted to be east or west of downtown. Weather wise it would be fun to be on the front of all the snow. The wind will be cold and at times rough. Pick a slip to point the bow North or West, which is the prevailing winter winds.
All said, I might consider living aboard up rocky river or something similar as opposed to being right on the lake. It should soften the problems.
Is the power of 2 hulls with you?
"Rainbow Flyer" - '86 Hobie Cat 18