He needs to militarily subject and autocratize America first.

You’re definitely overthinking this. IF such a deal was made, and that’s a massive if, the treaty would spell out exactly what happens to the people living on the land and those details would be points of negotiation.

Frankly the ideas of the other commenters that they would only be granted PR are ridiculous.

If we annex a chunk of land then we need accept the residents as our citizens. The finer details are an open question for treaty negotiations. I would guess there are requirements like it only applies to US citizens whose primary residence is within the territory at the time of signing the treaty, or at the time the handover occurs, or something in between. Maybe the residents have a choice: exchange American citizenship for Canadian, or keep American and get Canadian PR.

These questions are easily solvable but exactly how they’re solved is up to Ottawa and Washington. I doubt the US would ever give this land to Canada though, they will want something in exchange.

Why would you give them citizenship at all? They would be given PR status and we would probably offer to buy out anyone who didn't wish to become a Canadian PR.

Pretty easy, if they want citizenship they can do what every other American has to do.

Maybe I’m overthinking it though considering its such a tiny underpopulated area

^

Once they get their citizenship there'd be no particular reason not to use the normal rules around things like family. And according to the article half are dual citizens anyway.

You could make it so that anyone who was born in or had an address in Point Roberts for at least a year from the date the peninsula is absorbed into Canada is automatically considered a Canadian citizen.

I don't really have a reason to think there's more than average in that area.

Southwest Territories

The hard part is moving the Americans off it once we get it.

Just the blue states, please. We'll give them Alberta and Saskatchewan as a trade. (joking, of course. We need the potash, and probably the oil as well).