User blog comment:Zippertrain85/Why the Stormcloaks are not always right./@comment-17114085-20141111025602

2) It might take a few years but as soon as the war starts and the Dominion starts fighting the human races the Stormcloaks will start getting allies. Like others have said before, they have similar ideologies to the Redguards (Specifically the Forebears), they have already made contact with the Bretons, they are in relatively good terms with House Redoran (The leading Dunmer Great House in Morrowind). Just with those they have potential of getting 3 allies, which is more than the Empire can get.

The Dunmer and the Redguards are not on good terms with the Empire.

I doubt that the Empire would send another Legion to Skyrim if the Stormcloaks won the Civil War, unless the Dominion pushes them to. If the Dominion threatens the Empire with war if they don't send forces into Skyrim you can bet that the Empire is going to send forces into Skyrim.

Both you and me Zip know that Skyrim is in a pretty safe position when it comes to attacks from the Dominion. The only way they could get to Skyrim is by land or sea, both of which are extremely risky as they'd risk war with the other provinces before even getting to Skyrim.

So the only threats a Stormcloak Skyrim has is from the Empire, as I've said above, and the problems of losing some trade routes with the Empire. They'd still have the EEC, as that is a business that doesn't answer to the Empire (they sell to enemies of the Empire already, as shown by the fact Windhelm has a EEC warehouse even thought it is a Stormcloak city.), and they have the Dunmer. I also recall a ship in Dawnstar having just arrived from Hammerfell, meaning they also trade with the Redguards. So I don't see trade being a big problem for an independent Skyrim.

What is a problem is the fact they'd have to rebuild the province, fixing anything that was destroyed in the Civil War, and they'd have to train a proper army and get a proper navy, since they'd no longer have the Legion or the Imperial Navy. Guerrilla troops aren't going to do much outside of Skyrim. If they are going on the offensive then they need a real army.