I am strongly against including Hawaii. Not only is it misplaced on the map (It should be located far more to the left), but it doesn't lie on either the North-American plate, or the Caribbean plate. You could use [this](
http://upload.wikimedia.org/wikipedia/commons/8/8a/Plates_tect2_en.svg) picture as a reference.
Let's all face it: Hawaii is nothing more than a group of islands the Americans wanted because of it's strategic location in war, to supply ships and such. That's why they planned [the coup in 1893](
http://en.wikipedia.org/wiki/Overthrow_of_the_Kingdom_of_Hawaii#United_States), because America couldn't trust on the peaceful [monarchy](
http://en.wikipedia.org/wiki/Kingdom_of_Hawaii) that fared well for half a century there. Then, because it was not enough that the island was a [republic](
http://en.wikipedia.org/wiki/Republic_of_Hawaii) already gaining large influence from the Americans, [President William McKinley](
http://en.wikipedia.org/wiki/William_McKinley) decided it was theirs in 1898. In 1959, they "agreed" to become the 50th state. In fact, over the years Americans had already formed three-quarters of the population. The Hawaiian language corrupted, and all of the island's culture disappeared or got adjusted for tourism.
I bet they will do the same with Cuba in 5 or 10 years, as soon as [Raúl Castro](
http://en.wikipedia.org/wiki/Ra%C3%BAl_Castro) dies. They will "liberate" the country, and add it as their 51st state. And other countries can't do anything about it, because whoever protests gets a trade-blockade.
That's why I think you shouldn't add Hawaii to a North-American map. It will only remember to the American (read: American politician's) lust for power. And the map title will be meaningless, you should better name it "USA and some other countries waiting to be conquered". Hawaii should be added to an Oceania map instead. I mean, on an Europe map, are you going to add the whole of Russia? There's nothing wrong with leaving out a part of a country that doesn't meet the map's specifications.
And Iceland is something different. It could be added, since half of it lies on the North-American plate.
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And about the bonus values:
US: 25
Canada: 10
Central America: 5
Caribbean: 4
Mexico: 4
Just ideas, not orders.