New york? please. That's STILL not America. Have you ever been there? It's a cesspool of so many cultures, it might as well be an international trading post. Not to mention the smell. And no, the smaller english ships were able to maneuver in the storm, while the bigger and better spanish ships couldn't and they sunk
What's stopping my armies? A few hills? MY ARMIES COME FROM THE MOUNTAINS! Don't be silly. In open fields, the shield wall will do fine. I wonder were the Imperials got it from? Couldn't possibly be their Nord cousins to the North, who made the bulk of Tiber's army, could it?
Even IF I see a force that might be a problem? Why would I engage them? That's stupid. I fight on my own terms.
The combined navy of the English and the Dutch also outnumbered the Spanish Armada. Especially after the Dutch cut the Spanish of from any reinforcements.
At the time New York was extremely important, the language chosen there would be the language of the US. Also just so happend New York was founded as New Amsterdam, wich is why so many people in New York (and plenty of other areas) spoke Dutch.
The bulk of Tiber's armies consisted out of Colovian Legions. As have all the Empire's forces before his.
You think a simple shield wall is all you'll need against an enemy who has conquered the continent several times? And whatever you got planned, you'll have a hard time forcing the Legion out to fight on your terms.
Argonians, Altmer, and the Bretons would be my choice of an alliance. The locations of their provinces are beneficial to maintaining a strong presence on Tamriel. I am not too worried about how they'd communicate. The way I see it the Altmer, and the Bretons could work some sort of magical means to relay messages back and forth.