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.
I usually advise people to use Binance because it is almost the largest peer-to-peer exchange space, but I was surprised from sources on the web that Binance does not support Canada and you will not be able to create an account using Canadian identity. The information is not confirmed and you can search for it yourself.
It will be possible to give you better advice if you tell us the amount you want to exchange. If the amount is large, your best option is to use Bisq platform where you will find many traders who are able to transfer money to your account in the best way for you. You can also use bitcointalk forum if you want more options to compare later. In both cases, I advise you to divide the amount into small transfers to avoid being tracked by the authorities.
Binance supports most countries but there will be some countries with stricter laws, in which case businesses wishing to operate must register for a business license and be regulated separately. For example, in the US, US investors can only use Binance.us, Binance global will ban US investors. Canada is a pretty friendly country to the US so I guess they can use Binance.us instead of Binance Global like US investors. But as far as I know, the exchanges with better liquidity in the US are kraken, robinhood...binance is no longer considered the best option after what happened to them last year.
In countries with strict laws like the United States and Canada, encouraging people to find ways to evade taxes would not be a wise idea and would not benefit them if any accident happened.