Welcome later car!

Your budget allows for a decent bike and accessories.

Living in the GTA, I'm in agreement that you should consider a hybrid. Having a slightly more upright posture than riding in drops will help you navigate the Toronto streets with ease.

While I am partial to Kona-brand bikes, this time I would recommend you check out Mountain Equipment Co-op. They just started selling their own brand of bikes a couple of years ago.

I just picked up a discontinued last year's model Shadowlands from MEC for $250 off the list price. If you're lucky, the Toronto store may still have some on sale.

They also have bikes with internally geared hubs, which might also be ideal for Toronto conditions, including salt in the winter time.

Let us know what you come across and I'm sure the friendly people around here will chime in with helpful suggestions!