Yeah, I was thinking I'd likely sell through an exchange. My primary concern is that when I withdraw fiat from whichever exchange I use, the bank I withdraw to might want to put a hold on the fiat I try to deposit. Is this something to be concerned with? I've never tried before so I don't know for sure.
It is always best to err on the side of caution. I do regular crypto <-> fiat transactions and I personally prefer crypto friendly banks. And if I have no idea about a bank's stance on crypto, I try not to do larger transactions. I do believe some banks could have more friction with crypto.
I'm not from Canada though nor familiar with Canadian banks. I'd say you're better off asking a local. Maybe you'll meet some here otherwise you can try at r/BitcoinCA -- subreddit for bitcoiners in Canada.