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.
Essentially, you don't need to worry about the transactions that enter your account because when you use a P2P platform, you receive funds from a local merchant living within your country, as long as the sender doesn't add a note or something in the transaction mentioning anything about cryptocurrencies, that bank wouldn't know. However, as suggested by some other users as well, I wouldn't recommend selling a lot at once and receiving large funds because that might make the management ask questions about where the funds are coming from if the transaction is unusual.
All I said above applies to countries where Bitcoin is neither legal nor illegal, but even if banks aren't okay with such transactions, they wouldn't know if you receive such amounts usually. I don't know what the laws are in Canada, so maybe you should check that first, but even if Bitcoin isn't legal there, normal P2P transactions received from local merchants shouldn't bring you any trouble.
Make sure you use a trusted platform, and always ask the buyer to send the funds from his own account, third-party accounts could lead to fraudulent transactions and that can get your account blocked.