Belated thanks to all who responded; this was very helpful. It sounds
more plausible than I'd hoped, though not, perhaps, here in Chicago;
it doesn't look like there are any marinas providing year-round
dockage here, unless you can swing an outright purchase of a private
slip under a condo high-rise somewhere (and I get the feeling those
types wouldn't let a sailboat in just on general principles). Toronto
sounds promising.

Thanks,
--Eli