Not an expert, but a couple thoughts: (if I happen to remember when she's awake and free, I'll ask my wife, who I think is closer to an expert)
You are trying to fly at peak time, to a peak location, with short notice. This is going to be hard.
You have a predetermined destination and time-frame in mind, you aren't going to get the best deal ever.
You are flying from Canada, and using Canadian credit cards / points programs. Not as cheap to fly, and the rewards hacking is not as lucrative as the US.
When people talk about travelling around the world for free, they are probably accumulating shit loads of points whenever the opportunity comes. Then they see a cheap flight, or a point redemption bonus or something come up, and they take it. Claiming points when they are cheapest, and then redeeming them for the best deal will get you furthest. But that doesn't help if you want/need to be at a certain place at a certain time.
For example, fairly sure my wife is one of those people. It's not unusual for me to hear something like "we're going to Bora Bora" in a year and a half, or how about Costa Rica "next month", etc. (this has calmed down since we've had to think about paying for son's flight).
Also, an example of the Canada / US thing, and other things that help
Say you could get yourself to Buffalo. Picking arbitrary dates, for two people on Southwest flying from BUF to JAX leaving on Dec 22 and returning Dec 27, it costs $1000 (that sounds very expensive, but I assume it's that peak season, last minute booking thing). Say you have a southwest companion pass, that cost is cut in half because one person flies for free. You can, or at least could, get Southwest companion pass with two credit card applications, and a whole bunch of manufactured spending. In addition, since you would have ended up with a lot of Southwest points through your manufactured spending, so you could use the points inseatd of cash, and the second person flies for free. You are out no cash money other then the costs associated with the credit card applications, manufactured spending, and the airline fees/taxes. Again, you would have spent a shitload of points for that flight, so maybe not the best deal, but perhaps gives you an idea?
I'm probably talking out my ass, I'll forward this on to an expert for her opinion.
This is the kind of thing I gather, but I kind of like it better when free tropical vacations show up in my calendar in advance thanks to someone else doing this dirty work, and I only have to show up and look pretty.