Line up your choice of motorcycles first. Your ride and age are the two biggest factors for insurance. Since you are over 25, you should be in he sub $1000 range on a 300cc and down, possibly as low as 500 on a 200cc and smaller enduro.
Good choice.
Try
FortNine.com (they always have lots of well proced clearance gear), GP Bikes and Royal Distributing in Whitby have showrooms. Re-gear in Oshawa may also be worth a visit.
My favorite small cruiser is a Vstar (Virago) 250. It's light, handles well and is and geared specifically for beginners. They are also durable and inexpensive to fix.
If you don't pick a Virago, start with a used 250 in the make you like. Japanese beginner bikes are cheap and hold their value if you keep them in good order. Sell it when it's time to move up -- you will not lose money. The next step would be a 500 Honda or HD, or a 650 Suzuki or Yamaha. With your frame size, I'd be looking at the Suzuki S40 -- it's the lightest 650 cruiser and perfectly sized for your frame.