It's a reasonably long haul from Windsor into the city everyday, so you'll need something to cope with 130km per day using a combo of motorway (toll roads), freeway and normal city/surburban streets.
Given you will be on a learner's permit, I would recommend you don't consider anything less than a 200c scoot, and probably aim for a 250cc.
Liquid cooled engines such as the Vespa GTS250, Aprilia Scarabeo 200 or 250 will not only perform better than an air cooled equivalent, they will last longer.
You also need to seriously factor in the service intervals, the likes of Vespa or Aprilia have service intervals of around 6,000km, for you that is 6 services a year whereas some scooters have 3,000km service intervals which means you would have get your ride serviced every month!!
Obviously having 3,000km services would add a lot to your total cost of ownership.