I'm always looking at cheaper ways to get to Orlando for my family of 5. We collect tons of aeroplan points with a credit card and when I fly AC for business. Still, it's sometimes difficult to cash in AP points for YHZ -> MCO.
Driving to Bangor is looking tempting, though I've never tried it. About 7 hrs from my place, one way. But there were some great deals last time I checked, and the taxes are less. I'd have no worry about doing that other than arriving on time for the flight, and finding parking (and the $$$ for parking); buying tix in the U.S. isn't much different from Canada. I think lots of NBers do this.
I've used google maps to estimate driving times, but I don't think we could handle it. The extra days in Orlando make the price of flying worth it for us.
We've used United, US Air and Continental, and we've never found any difference between them and AC. Never been on WJ or CJ.
Typically, we book 3 tix with AP points and pay for 2. But I might try booking 3 tix with AP, and then try another 2 tix with AP within 24 hrs. There are never 5 AP econ seats on any AC flight.
Also, I might try booking star alliance partners with AP points, but I haven't figured that out yet.
In winter months, there are more direct flights out of YHZ which is much more convenient, but I'll take a connecting flight if it's cheaper. I think the best time to go is Sept or Oct, but that's tough with school.
The only other advice to consider is booking early, but make sue you can change your tix (usually for a fee, find out how much and write it down). If you find a cheaper arrangement (more than enough to cover the change fee) then re-book. This also applies to rental cars and hotels.