If I wanted to skirt (or flout) the law, there would be much easier ways to get it done. However, I tend to think about the worst case scenario— is the risk worth the worst possible outcome?
For example: in our state, the legislature decided to (kinda/sorta try to) close an enormous budget shortfall by raising registration fees on everything in the state. Everything went up, but most egregious increase was light trailers. An “A” plated trailer (<3000 lbs) registration went from $18 to $118. The ticket for pulling a trailer without a plate is not a moving violation and $100 fine— but they never levy the fine, they just ask you to go get a plate. I don’t lie when I get pulled over, I explain my thinking. The risk of a ticket I’ve never gotten is worth the return of not giving this state another $118 to fritter away, because I pull a size small trailer once every couple of weeks. Given the laxity of enforcement, and the economical potential fine, I wonder why would anybody ever buy the overpriced plate?
On the other hand, bootlegging a vehicle from Canada, falsifying the documentation, and probably skirting all of the customs and sales tax would net someone in the US a really nice car. However, if the fraud is ever discovered, the result of that little act of personal libertarianism would certainly be the impounding of the vehicle, to say nothing of a hefty fine. It would also be a felony or three. If you could stay out of prison, the legal fees would bankrupt you, and the publicity would ruin you. Or, perhaps you just take your lumps in the big house for tax evasion and fraud.
Alternatively, maybe you get away with it and nobody ever knows. I wonder though, what happens when you get in a bad wreck (one where liability is assigned to you). Insurance investigators are not stupid-- they’re going to figure out that the car isn’t what you said it was. At that point, the insurance company is off the hook for the damage you've caused, and everything falls back on you. I don’t know about you, but I like the house I live in, and I’d like to keep living there.
Maybe you never got in a wreck. But once you falsify the paperwork, how do you ever sell the car? I probably never would sell, but I doubt that my heirs would be all that interested in a very expensive replica of a car they don’t care about after I'm gone. In the event of my demise, I would be exposing those I love to a felony charge if they perpetuate the fraud, or a complete mess (straightening it out) if they don't. It just kicks a hornet's nest in their lap. That's not how I'd like to be remembered.
Lastly, as much as stupid government stuff like this really sticks in my craw (and it really does stick in my craw to an enormous extent), there is the moral problem of lying about something to get what I want. I’m presented with this opportunity multiple times every day— to cut a corner here or there to get what I want. I don't do it in small things, why in the world would I do it in something this big? Sometimes I feel like a sap for not just doing what everybody else seems to be doing to get ahead. But I really do believe that I’ll answer for every one of those cut corners in this life or the next.
As much as I want this car, it’s just not worth it.