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I have a Kindle, but I've also gotten a number of books from the B&N store, so:
1) Both. I'd advise registering the account with your Florida address. They flat-out won't let you pick up certain books without a US shipping address, and the Canadian-compatible selection is limited.
The IP question is a bit tricker. Currently there are a few books available for both Canadian and US addresses. Generally, if a book is US-only, then the purchase will fail if you don't do the US proxy dance since apparently they check your IP during the actual checkout.
On the other hand, I think I've clicked on a couple of freebies once or twice when I've forgotten to load up the proxy and they've gone through okay. But then I live pretty close to the border and whatever they use for geo-location might be lenient in that respect.
3) I have nothing really to base this upon, but I say get the Wi-Fi model and save your money. By the time the Nook's officially supported in Canada, they'll probably have a new and improved version at an even lower price. Or our dollar will have gone up again, effectively lowering the price.
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