A Honda Shadow will be nearly bombproof, they're pretty much the quintessential Japanese cruiser. Though I will say, carburetors need a little more attention for the winter storage I imagine you'll be doing in Canada. Just don't store the bike for months at a time with a full float bowl unless you've put some Sta-Bil or other fuel stabilizer in your last tank before you put it away for the season. Fuel-injected engines are a bit less susceptible to this, but it can still cause injector clogging.
I really don't know the market up there, but Honda and Yamaha cruisers are good bets, Older Yamaha cruisers might go by V-Star up there like they were here for a while. I started on a small-displacement Yamaha cruiser, I'm on a modern Honda 500cc naked bike now, it's been excellent. I commute on it year-round.