Well, historic connections or the lack thereof notwithstanding, there has long been limited interest in Canadian political circles about annexing certain places in the BWI.
Canada’s strange quest for its own Hawaii
As you can see from that article, nothing has ever come of these proposals, but they continue to be entertained, most recently at the NDP convention in 2016. So, I would not say it's total ASB.
As for how Canada would look today, well, obviously more people from the Caribbean would likely be living in "the Upper 10". I'll also be a little bit negative here and say that anti-black racism would be more of a thing in Canada, especially if the new provinces were viewed as benefitting from Canadian "generosity" while not pulling their own weight. (Check out the comments section of any Canadian news article about First Nations people to get an idea of what people would be saying about West Indian Canadians. Not pretty.)
I'd also predict there might be some resentment among Canadian First Nations themselves,some of whom would be thinking "Hey, a lot of us are still living in conditions that are third-world, why the hell is the government doing anything for the Caribbean before they've solved our problems?!" If the islands were brought in as full provinces, it would cause quite a bit of conflict with Yukon, the NWT, and Nunavut, all of whom are currently expected to make do with territory status.
Politically, I'm wondering if West Indians who voted for people like Michael Manley and Maurice Bishop would throw their support behind the NDP(who were the party debating annexation in 2016), or if they would just fall into the usual Canadian habit of swinging mostly between the Liberals and Tories, with occassional stops at the NDP.
