Second does no one like to remember that Gen Tullis says that he is getting no reinforcements from home?
I would just like to point out that Reinforcements means large bodies of men to aid or relieve standing troops or to provide frontline support for engaged areas. It does not cover the full scope of support. While the Empire may not be sending Tullius legions and units of considerable numbers it would be plain dumb to think they're just sending him post cards. "Wish you were here." "Good luck with the Rebels!" I have zero doubt in my mind that he can requisition mages and veterans to train and operate in his army in small, reasonable numbers. That's why I said he has manpower trickling in. But even ten mages from High rock or a half dozen Bosmer archers from the refugee Valenwood legions coming in to help every couple of weeks is a distinct advantage and a great aid to the regular recruitment that both sides have to rely on.
That being said those wanting their freedom will make it too painful for thos who want to occupy. Thus the Stormcloaks should win. Look at Rome trying to hold the british isles, in time they lost to the barbarians because it was too costly to stay.
You're forgetting that the Imperials are nedic breeds that came from Skyrim. Skyrim wasn't occupied or FORCED into the Empire. It WAS the Empire. When the Cyrodiilic Empire formed the nords considered themselves a part of it. The Empire was formed in the lands of Cyrodiil but born in the lands of Skyrim. So the Empire isn't an occupying force. That's especially naive to say when you take five minutes to realize that 70% of the Imperial Legionnaires in Skyrim ARE nords and they are fighting for their homes as well. As far as they're concerned Ulfric is the one trying to take from them the government THEY want and the way of life THEY want. I mean take a good hard look at Solitude compared to Windhelm. Which would you prefer to live in? Solitude, funded by Imperial trade and thriving off it? Or Windhelm; oldest city in Skyrim and it SHOWS?
On that subject, let's consider what would happen to the individual holds, shall we? Let's say Ulfric wins. Well now Markath is screwed. Its primary export is Silver and with the Imperial trade driven off that Silver goes to other holds. But an isolationist government without export will eat away at itself and eventually die. You can only circulate money so long before you need new income from outside. Even CHINA knows this and they're as isolationist as it gets. Whiterun under Ulfric's rule becomes the breadbasket. Without any foodstuffs coming in from the rest of the Empire the Nords must become completely self sufficient. The lands in the frozen north have very limited farmland. So many nords in Dawnstar and Winterhold begin relying on meat as the cost of bread becomes astronomical while Whiterun strains itself to feed a nation almost by itself. These meat diets lead to more meat cooked, more animals killed. And once they've hunted themselves out of food the northernmost holds will start to fall into a light famine. Causing an exodus. Those that leave them arrive at Solitude and Windhelm. Forcing these cities into a crunch for food and water. And Whiterun, whose populace is already rationing grains and in which the quality of life has dropped dramatically as farms are forced to give away more than three fourths of their crops to feed Skyrim and the economic downfall of no longer being able to sell these crops for needed materials, can no longer support all the holds.The Rift, completely free of the threat of Imperial attack, becomes a center for corrupt officials. The Silver being circulated from Markath is horded by aristocrats that control Riften's people like puppeteers. Engaging in underworld trades with Imperial contacts to procure luxury items that they then bilk the general population for to further horde money. Windhelm becomes a massive expense as Ulfric would no doubt wish to see his home city restored to its former glories. So the kindly peasant class finds a large number of themselves working in quarries for very little pay. But hey, with the silver economy dwindling at least it's work right? They might see their families again someday. Maybe. Anyone with a bit of college can tell you working in a quarry during the iron age was like gambling with your life every day. And a lot of people lost.
Now you may ask "If it is so doomed how do you explain Skyrim supporting itself in the earliest years, Will?" And there's an answer to that. Expansion. Under Imperial rule Skyrim was in position to receive great benefits from the Empire. Food, materials, trade, et cetera et cetera. During that long LONG period the added benefit of the Empire bolstered Skyrim. You have to use your imaginations. Cities wouldn't be composed of two or three dozen people as the game displays. You have to imagine there are more beyond the walls you are within. In other worse Whiterun is THOUSANDS of people. Solitude is tens of thousands. And the influx of Imperial wealth and resources during the first couple CENTURIES encouraged this growth. Skyrim was self sufficient before it was a multi-cultural land that traded with the whole of Tamriel for goods and services. If they try to stand alone the nords are faced with 2 options. 1) Kick everybody who is not a nord out, eliminate 65% of the local luxuries and return to a basic way of life in which everybody worked twice as hard to scrape out half as good a living. Nord or not, best of luck getting an entire CIVILIZATION to be okie dokie with that. Imagine someone coming into your house and saying no more internet or TV, we have to spend 7 days a week working 10 hours a day to be sure our crops come in well enough to feed our family and have enough to turn a profit to purchase things we can not grow. The vast majority of people would be a bit pissed. Option 2) Trade outside Skyrim. But Argonia has very little the nords need and Hammerfell is... a desert. They'd certainly be willing to BUY from Skyrim. But in terms of bringing things INTO Skyrim? Sorry. The stuff Skyrim would need would be either in Imperial or Dominion lands. So congratulations Ulfric. You won! Now your stupid ass has to try and play nice to trade with the people you have been spitting on. Best of luck.
You can pretty it up with speeches and propaganda all you like but bottom line is: Stormcloaks bad. They don't know it. They don't mean to be. But they are bad for Skyrim.
And they would not win. They just haven't got the mixed unit versatility that the Empire has. They are rigid. And EVERY Rigid force in the HISTORY OF THE WORLD has lost to a more fluid, modifiable and adaptable military. Vietnam was a great example of rigid military tactics being unable to beat an enemy with a dozen tricks. Iraq is a great example of how a more versatile and prepared military can root out and eliminate even the toughest of enemies gone to ground.