Craigslist is a good place to find cheap and used scooters. Vespas and others too.
A scooter is very handy downtown, and sometimes in suburban areas, but a little more dangerous, since cars outside of the core are generally used to large open spaces, they will NOT see you on a scooter.
Motorcycles are great, a little tougher downtown cuzza traffic and most being air-cooled, although ones that are liquid-cooled are good.
As for learning a bike, it's easy, driving standard in a car has the same dynamics as a bike, although you'll likely stall a bike a lot fast and a lot more than a car, since the clutch and throttle are a little more sensitive, and because you reach the higer RPMs a lot faster.
Motorcycles/scooters can basically park anywhere and not get ticketed, PROVIDED it's not on private property and it's still avoiding important traffics areas (Yonge St).