Bethesda has done a wonderful job at making the civil war a hard decision. In fact if they were to have a 3rd peaceful reconciliation option instead of one side vs the other, I am almost certain that would be the most popular BY FAR.
(Kind of miffed that isn't an option Beth!)

So it comes down to an independent Skyrim kicking the [censored] out of Thalmor out of Skyrim, which is a VERY attractive outcome.
Though having a less than fully weakened Empire to one day [censored] the Thalmor in WW2 is also VERY attractive.

Though Hammerfell is likely to aid the Empire in a war against the Thalmor, would Skyrim do so as well? The Empire didn't outright make war with Hammerfell, and Stormcloak is the rightful high king of Skyrim in accordance with the old nord ways.

Oh and the Empire tried to cut off his head. So if Skyrim became independent, how would Bethesda write that into the lore, unless the next great war happens in a few generations after Skyrim takes place?

Also which one is more likely to be written as what officially happened? Its not like one is more obvious than the other. Unless the next tes game just doesn't mention much about the civil war other than a vague footnote?

The civil war will be rendered null five years from now by an infestation of space-gerbils. Don't ask how they got there, the Elder Scrolls told of their coming.

The Thalmor lose either way. I'm almost certain we'll have a DLC where we "finish the fight" so to speak.

The Empire is dying, with or without control of Skyrim. Eventually regardless of how the war turns out, Skyrim will become an independent nation I feel.

Another 200 years is quite a bit of time between now and the next game where Bethesda can think of something clever that puts either one in power no matter how we ended the game in Skyrim or whether some other event happens like a meteor impact

The same way the major house of Morrowind was handled. Nobody gives a crap.

I still believe the game is setup so the Dragonborn becomes the new Emperor. An Ulfric Skyrim will join this reformed Empire as it fulfills the ideals the Stormcloaks left the old one over. An Imperial Skyrim will have never left the Empire in the first place.

I think that what will happen, no matter what side you choose is that Skyrim will remain within the Empire but have major concessions given to it, with or without stormcloak victory. So for example they'll say that 'After the Stormcloak rebellion Skyrim remained a part of the empire but had religious freedom etc' So you don't know who really won, and because the empire is going to go to war with the Thalmor again anyway (It's very heavily hinted) if the Thalmor were booted out and a war begun it wouldn't have been stopped if they hadn't of been booted out.

I think in Lore the Stormcloaks will win.

Well, it was a hard decision until...

Can you tell me the name of the Mane of Elsweyr? No? That's because it's not really on a need-to-know basis for the player in a province that isn't Elsweyr. Same goes for the outcome of this civil war. It won't be mentioned how it ended for Skyrim because it's not relevant for future games.

The lore will simply say that the Dragonborn ended the civil war in Skyrim, which led to the eventual reunification of the Empire. If the Empire wins in Skyrim then obviously reunification happens right away; if the Stormcloaks win then Skyrim rejoins the empire on its own terms afterwards.

werent there about 5 different endings to daggerfall?

That kind of works quite well, both outcomes can be supported tentatively.

If you believe that, then you misunderstood what "asset" means.

The lore would reference a civil war that weakened the realm to a point that made them an easy conquest, most likely Aldmeri Dominion. There is no winner of the war in this event.

My only difficulty with this point of view is that after the battle for red ring (the retaking of imperial city), the aldmeri forces were weakened as well. But the clear bias in their favour still shows them to be the more powerful force which forced major concessions from a dying empire.

There are other continents mentioned in lore I believe, but they remain mysterious and unknown, so perhaps a future threat will come from there.

"Remember the Stormcloak uprising in Skyrim?"
"Indeed, I do. So many dead, but at least it saw an end."

Being very vague and very general, while still mentioning it, is the way I predict it will occur. It's not to hard if you flex your writing muscles, and it will keep almost everybody happy.

You misread that.

I know what it means and I read the entire document. It makes the choice pretty easy.

There's a difference with reading and understanding. You have it completely and utterly wrong. The Thal don't want Ulfric on the throne as much as they didn't want the Empire to have control.

Derp.

I understand that, however if one must choose, it makes it easy. Read my reply to the other guy.

Again, no. The document says it's a SLIGHTLY better outcome than the Empire holding control. They still state it's bad if Ulfric succeeds.

Ulfric HIMSELF says they;re preparing to attack the Thalmor. Have you even completed the Stormcloak questline? Or are you just flinging nonsense around?

Easily if it doesn't take place in skyrim. Also canned npc responses can be coded in the new land or unique npc occurrences depending on the side you've chosen. Honestly games have gitten around this. Including fallout 3

If I had to guess, I'd say the Stormcloaks will win in the canon.

Obviously some spoiler stuff here, and I can only talk about what happened on my play through when I chose to be on the side of the Empire:

Killing Ulfric doesn't end the civil war. NPCs still talk about it, Stormcloaks are still all over, and there has been no Moot to determine the next High King. The game does not show the true end to the civil war, so it can be tied up later either in DLC or lore between games. I'd say it is canon that the Dragonborn brings an eventual end to the war, but whether or not Skyrim rejoins the Empire will depend on where/when the next game or expansion takes place.