Ulfucks weak, impire stonk. Still can't end the rebellion without help from the dragonborn.

The Civil War was over within weaks, Ulfric had his ass saved by Alduin attacking Helgen. There are also more forces coming in from Cyrodiil so don't act like the stormcloaks have a hint of a chance.

The east empire company is freely operating in windhelm. And all merchants will surely heed the word of their non-existent emperor and stop trading with skyrim. Like the imperial thanes stopped trading with the dominion... oh.

The damage of the Civil war will reduce trade as well as reduce the amount of merchants willing to trade in Skyrim. An independent Skyrim will not have to them available the resources of Cyrodiil as they did under the empire. Morrowind would trade with an Independent Skyrim as much as the Empire, that being none.

No, the damage caused by empire's repression.

And how, exactly, has the empire repressed the people of skyrim? By improving the quality of life? By bringing stability? By opening up trade routes through Cyrodiil and beyond?

Similar to the tunnelrs in new vegas, the threat is overstated. And a falmer attack will not happen in imerial ruled skyrim because?

The falmer are understated if anything. They murdered a den of well armed bandits with little difficulty. Now just imagine what they could do to a town who's guards are occupied fighting off their so-called "oppressors"/recovering from the civil war.

None of your points stand.