If you go to expedia.ca, you can sign up for what they call "My Trips", and it will track the fares for up to three different destinations (I think travelocity offers a similar service).
Once you're signed up, it will keep track of the lowest available fare offered to those destinations (the price they show is before taxes - which can add a good chunk to the fare). They will also periodically send out an email letting you know what the lowest fares are for your choice destinations too.
I live in Calgary and have been tracking the fare from Calgary to Orlando since January for a trip this fall (I assume the prices from Edmonton would be similar to those from Calgary). Regular price after taxes from Calgary is in the $800-900 CDN range.
Air Canada has been having pretty frequent seat sales lately, so you can usually find the fare for less than regular price if you wait it out. The problem with waiting for the seat sale is they usually only offer the rate a couple of months before your trip - sometimes a couple of weeks if they really need to fill the seats.
I've seen the rate from Calgary swing quite a bit in the last three months, from about $300 before tax to close to $500 before tax. Imagine my shock last week when I went to expedia and found the fare to Orlando was cheaper than either LA or Las Vegas (my other two places I track the fare to) - about $265 before tax. It was so low, I figured it must be a mistake. I was able to book my flight after tax for about $370 CDN return - less than half the regular fare.
I never saw this fare advertised anywhere and wouldn't have known about it without the fare tracking on expedia. Of course, how did I thank expedia for their help? By booking the flight directly with Air Canada - which saved me about $10 more.
I would watch the fare closely, decide what your budget will allow and then grab it once the price gets to the point that you're comfortable paying for the dates you want to go.
You say your dates are flexible, which will make it easier to find a low fare. The fare I got was restricted to Saturdays, Tuesdays, or Wednesdays.
I noticed that you live in Wainwright, so you might try tracking the fare from Saskatoon and Calgary too. If Edmonton is $800 per person before tax and Calgary is $800 after tax, you might be able to save quite a bit of money for just a little longer drive (you could probably even take a cheap WestJet flight between Edmonton and Calgary and still come out on top).
I used to live in Lloydminster and drove through Wainwright many times on my way to Calgary, it's a decent highway pretty much all the way even in some bad winter weather. It might be worth the extra drive if the savings are good enough. On the other hand, the roads in Saskatchewan are horrible in the best of weather.
About booking the room, from what I've read, January/February is the slowest time of the year around WDW (except for Presidents' Day Weekend - which is the same weekend as Family Day in Alberta), so I doubt you'll have a problem getting a room on-site during that time period unless you have a very specific room request (someone who's more familiar with things can correct me if I'm wrong).
In my case, I was thinking about going later in the year - between Canada's and the US's Thanksgivings but the rate I found was so good and only available through the middle of October that I bit the bullet and decided to go in September. I hadn't even thought about what to do for a hotel - then Disney rolled out the Fairytale Magic plan and it was like a signal from above.
Two weeks ago I was still contemplating what to do, now I've got everything booked and 133 days to kill.
