That is the street price from my pharmacy. The price will differ a bit from pharmacy to pharmacy, as pharmacies charge a dispensing fee. So, it tends to me a bit mores pensive at Co-op than Walmart. Maybe $15 more. However, the insulin isn't subsidised by anyone. The government doesn't subsidise insulin, but rather it regulates the maximum price a patentee can demand for their product. You can read all about drug
price regulations in Canada here: http://www.pmprb-cepmb.gc.ca/en/regulating-prices/regulatory-process
Canadian pharmacies also are not required to jack up thei prices to sell to Americans. Whatever websites you are consulting are trying to make a hefty profit off of you, and I wouldn't order from them. Most of those companies that specifically target Americans raise the prices considerably and won't even actually sell to Canadians because then they wouldn't be able to get any where near the profit margins that they get when selling to Americans. Somewhere like Mark's Markne Pharmacy does in fact ship to Canadians, which is a dead give away, that, while they do raise their price some ($150 for 5 pens vs $75-100 depending in where you go, they aren't doing it to the extent of those other pharmacies, but rather much more like other online pharmacies that also sell to Canadian, like Diabetes Express. You pay a bit more for the convenience of not having to your house. But not hundreds of dollars more.
As far as actual diving up and buying insulin from a brick and mortar store, going over the boarder with it shouldn't be an issue. Insulin is OTC here (so acquiring it will be no problem) and while prescription in the US, CBP and TSA only require a doctor's note or a copy of your script, that the medication be available in the USA, that it be in its original container, and that you don't bring in more than a 90 day supply for your personal use. The rules are here: https://www.fda.gov/ForConsumers/ConsumerUpdates/ucm484154.htm
So I don't think driving up here to buy insulin is really walking that fine a line, provided you have the necessary documentation. Perhaps I'm misunderstanding something and you could clarify?
Aw far as actually importing it from online, like I said, being Canadian, I know that it is legal here to sell to Americans, but other Americans should advise on the legality of importing it state side. Or do their own research.