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If you have a car full of brand new luxury goods going into the US, customs and border patrol are absolutely going to pull you in for further inspection and questioning, and they will make you pay the tariffs. They were incredibly shitty to me every time I crossed as part of my job a decade ago, I can only imagine now.
Also if/when they catch you, you're now on American soil and dealing with their legal system, they're not going to just turn you around and let you go back into Canada.
It'd be effort but this is why I say go for parts. You gotta get somebody to know what are common parts in industrial or other machines that are, basically, only made by about 2 factories in China at most. That can't be too hard. Then you need to network inside the US to see where you can flog this shit. I don't think the customs is gonna bat too much of an eye at an industrial grade 10" roller bearing Type H3B and other such bullshit if you only bring in handfuls of each.
Or you know, abuse the culture wide blindness to bicycle parts and smuggle in high grade bicycle equipment just rolling around in your trunk, they're not gonna know what a Roloff internal gear hub or a XTX derailleur is if you take it out of the package and shit's just rattling around in the trunk, probably.
I don't think the customs is gonna bat too much of an eye at an industrial grade 10" roller bearing Type H3B and other such bullshit if you only bring in handfuls of each.
You are severely underestimating how shitty CBP is lol. I've had a few especially shitty border cops over the years question shit like basic tools I had in the trunk of my car. I had friend who ran conferences, on a trip down for personal stuff he brought a pretty standard DSLR and a tripod to shoot an interview with someone who was gonna be at one of these conferences while he was there anyway. He didn't admit that and just said it was for taking pics of the trip, but they didn't believe him and said that he was smuggling in equipment to do work in the country, and detained him for like 4-5 hours, during which they scoured social media and found a youtube page for the conference stuff. They didn't have any proof but that didn't matter because they have a right to refuse entry, turned him around and banned him from the country for something like 3-5 years?
touché
Estrogen... Bring us lots and lots of estrogen.
Oh fuck, estrogen is an import? 
Most pharmaceuticals are... But the majority are actually made in India.
I think some Americans who live closer to the border are already considering that. Fun fact, many folks in California have their dentists in Mexico for this reason to dodge porky’s price gouging.
If I were to spitball, if you live in a major city like Toronto or Montreal or maybe smaller places of significant touristy attraction like Niagara Falls, I wonder if if would make sense to start a ‘tariff-free shopping tour’ and sell tickets for them to join you.
Can confirm, especially if it’s just over the border, but even with a plane ticket, the dental will still be cheaper
I would try to cultivate a relationship with some type of independent business that makes bulk purchases of items where Canada has a regional production or trade advantage, but where no one will care about a grey market. so, not communication technology with license agreements. but probably stuff like storage devices and equipment.
smuggling is relational. it's about being a middleman, limiting your crossings, making them count (high volume) and using a contact on the other side to facilitate distribution.
off the top of my head, beyond the tech sector, I think maple syrup and maple syrup production related equipment could be something.
might be good to think of something that people will want regularly, so they have incentive to keep the relationship going and not burn you for some reward.
as your attorney, I advise against this because customs enforcement are the American gestapo and they are on one even more than usual.
Hockey equipment too....
Trebuchet.
Tunnels chapo