I'm happy to offer advice, but I do expect you to get off your duff and use Kijijij search to find the bikes yourself.
Unless you have other (questionable?) plans for insurance, I bet that will be the limiting factor for insurance. It's also why most people your age start on CBR125's and Ninja 250's and there's no shame in that. Personally, I started in my late 20's with a 600 sport-tourer, both of which helped with insurance (not that it was cheap!)
Anyways, good luck.
Have been on kijiji everyday but I keep hearing these stories of magical bikes that only some forum members have access too that are cheaper and better than anything I can find "apparently".
Insurance = not an issue, fire away.