I'm at Toronto Island Marina and I know for a fact that there is a couple of live-a-boards here all year round. I know that Lakeshore Yacht Club also has a few all year people. The rule (law?) is that there has to be 2 boats as a safety measure for each other. Try calling Lakeshore. They may know.
There are liveaboards at TIM year round? And they can live on their boats out of the water? Hrm. Seems I've been misinformed.
Lakeshore is a bit far for me. I was hoping to live at TIM in summer and Harbourfront Centre's Quay West in winter.