Just thought I'd post an update since I originally asked this question and just got back on Tuesday. My sister ended up driving me to the airport in Orlando, it took 25min to drive from the POR to the airport, I got there at 6am, there was no line-up at the Air Canada counter, security check in (where they only looked at my ticket and put my purse and carry-on through the x-ray, didn't even look inside them) and I was at the boarding area for the flight at 6:15! The flight did leave a little early because everyone had boarded and it wasn't very full.
We also had great luck at Pearson on the way down, we thought we were late so parked right at the airport, there was a big line at the check in counter and I was the only one with a executive class ticket but they let all of us (3 adults, 2 kids) check in at the executive counter, then when we got in line for the US customs an employee saw us with the kids and pulled us out of line and took us to the crew customs check, then they let me board early with the kids too, even though they were in the regular section and I was in executive.
I was also the first one off the plane on the return flight so that went really quickly too, although the Canada Customs guy seemed a little suspicious that I was travelling by myself and went to WDW for the weekend!