Again, if Cyrodiil is as bad as you say, why would they have to travel by coast at all? The more troops the empire sends to Skyrim the easier it will be to take. If they are successful in taking the central province than it's only a matter of time till they have enough resources to utterly crush Skyrim and Hammerfell. As for Morrowind not being friendly with the Aldmeri, they may not be pals, but that doesn't mean they'de side with Skyrim in a conflict, not when the Nords seem to despise them and if the are successful in succeeding from the Empire than they'll have a fascist king. While I agree that Morrowind is not part of the Empire or Thalmor, since the destruction of Red Mountain and the removal of it's heart it has ceased to act as a pillar of reality, so the Thalmor's main interest with the country is the potential military backing and ensuring Talos cultists are unable to evade them by fleeing their. With that in mind I think the Thalmor are working their agents into power in that country like they have in all the others. They aim to unravel reality and cast it back into the spirit world, and this goal can only be achieved if they are able to succeed in getting rid of Talos. Heck, maybe the graybeards are Thalmor empathizers, they do after all tell you to let the world be destroyed by Alduin.
Well, I'm only outlining the naval situation because it seems to be a strong argument for the average imperial supporter.
Also, the Dunmer seem very. very uninterested in the Thalmor, why do you think Malborn fled there? Even so, they've still not recovered from the Red Year. My bet is that the best they could do is occasionally raid the border.
"The more troops the Empire send to Skyrim, the easier it will be to take". Are you talking about the Empire, or the Thalmor? That just seems out of place.
However, warfare is more than numbers. in fact, numbers can be a severe weakness. If a general becomes complacent in the fact that he outnumbers the enemy 10 to 1, he will fail (Cannae, for example).
And i suppose I'll nitpick about the fascist king part (if you don;t mind



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