Most of Canada's oil is heavy oil that doesn't compete well with the lighter oil on international markets due to difficulty in transportation and refining. It is shipped to the US by train, and refined in the US which has costs associated with it. I couldn't find a source saying that Canada would be 20% better off shipping to our other export targets like the EU. I'm willing to be taught a lesson by such sources.

I'm guessing you're arguing that trade with the US makes drugs expensive. Canada protects drug prices as part of our single-payer system. We negotiate prices nationally and thus pay close to what other OECD nations pay. Re: patents - I could very well be missing something, but wouldn't such patents exist regardless of trade agreements? If we could buy generic analogs of patented drugs then surely we can regardless of patents. If we can't get generic analogs then how does cancelling trade agreements make patented drugs cheaper? If you are just saying that US big pharma sucks then I totally agree, but I don't see how ending our agreements fixes that.

Americanization of media and culture isn't just a Canadian problem that stems from our close relationship to the US. Things like radicalization and swings towards autocracy are happening in democracies (and other systems) all around the world regardless of level of direct US influence. I don't think it's fair at all to say that if we didn't associate with the US that our society would be free from US-style problems.

I can see that NAFTA has caused instances of ignoring environmental damage. I will say that as far as I can tell by looking it up, the Lone Pine Resources v. Canada case was decided against the corporation, in which case the destruction you mention was not allowed. "On November 21, 2022, the NAFTA tribunal found that revocation of mining rights around the St. Lawrence river did not amount to an expropriation, considering that Claimant retained other mining rights. Tribunal majority also dismisses MST claim." Unless I'm reading that wrong (definitely a possibility) in that case NAFTA officials actually stopped environmental damage. Plus let's face it, provinces like Alberta and Ontario do not need NAFTA pressure at all to make large-scale environmentally harmful choices. I'm not convinced Canada would have refused to exploit resources if free trade wasn't a thing.

As far as the relationship being shit, there's a lot of experts who say it's beneficial. If nothing else it has created TONS of jobs for Canadians and been a bedrock of our economy across many sectors.