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It looks like the LSOB is very close to Eglinton subway station on the Yonge Street line (also known as the Yonge-University-Spadina line). There are many buses that go east and west along Eglinton as well, so getting there by transit should be easy. You will likely want to get a place in the north-central part of the city.

TTC transit system map: http://www3.ttc.ca/Routes/General_Information/Maps/System.jsp

what is the Zipcar?

Zipcar is a car sharing service where you can rent cars located in various parking lots around the city on an hourly basis (around $10 an hour including gas and insurance). While a regular car rental agency is probably better for multi-day rentals, it can be quite cost effective to use for short journeys around the city (such as for shopping).
www.zipcar.com
 
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I find that the cold isn't too bad... unless it's windy. And if you're going to ride a scooter or bike, you're going to get a lot of wind in your face and if it's under -10C it will be painful for any exposed skin. It's mostly really bad in January and February, although the windchill can be unpleasant in December and March. It's interesting seeing some of the hardcore cyclists in Toronto in the winter, a lot of them look like they're going to rob a bank with ski masks, bandanas and goggles.

The biggest problem with motorcycling in winter is not the cold by the ice. Two-wheeled vehicles need lateral traction in order to stay upright. Riding a bike in winter is possible because your weight, speed and power output are relatively low so you can often see and avoid icey patched or if you find yourself on ice you can put a foot down and slide across it. On a scooter or motorcycle you are more constrained in how you can avoid ice on the road, and you have a lot more momentum (speed and weight) meaning you can't always get your foot down safely to stabalize yourself. If you're going to ride a motorcycle in winter you need a sidecar.
 

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