We are in Italy on an Elective Visa--and were fortunate to be able to use the consulate in Houston. The various consulates are quite different when it comes to "user friendliness"--and some of them are a nightmare. But you have no choice--you have to go to the one designated for your state.
Plan on going twice--going the first time with everything you can possibly think of--with copies (they usually will NOT make photocopies for anyone), with flexibility in your schedule to return soon thereafter with whatever they say you need. You are right! You may THINK you know what is required, and then they throw something else at you. And no one else's experience can truly prepare you for yours.
Two examples:
we were positive we needed to show proof of medical insurance. We have NEVER heard of anyone NOT needing this. The woman in Houston said we didn't need it because we would be getting residency in Italy and then paying our way into the Italian health service. (She was correct... that is exactly what we did.) But we are the only people we have met or heard about who did not have to show proof of medical coverage.
when we came back for our second visit.... she said to bring with us the photocopy of our airline tickets for the trip we would make to go to Italy. I had never heard of that one before. We asked her if she was confident that we would get our visa in time for a flight by a particular date (like 2 weeks away), she said yes, and so we purchased tickets with some trepidation, and brought the receipt the next day.
We also heard we needed fingerprints and criminal checks by the FBI. Nope! She didn't want that. Nor did the questura in Siena after we arrived.
So--embrace the unexpected! That is what life in Italy is all about. In bocca al lupo!
(I don't think flying out of Canada is a problem at all.)