Even despite all of the BS Ulfric owns as a character and no matter how marred his legacy will be due to his actions (and inactions), I am glad to see that the man isn't a Terminator and
seems to at least feel some level of concern and shame relating to all that's happened.
When asked by the player character about taking out the Emperor on his visit to Solitude, this is how he answers:
We're ready to march on Solitude, but the Emperor's
cousin is getting married! If royal blood was spilt, all of
Cyrodiil would be up in arms.
We can't afford an all out war with the Empire. So we'll bide our time for now.
While it's good to see that he's got the ability to think ahead to
some extent, it also strikes me as odd that he wouldn't think that his rebellion could very likely have the same effect. It's a huge gamble he's taken by killing Torygg and igniting rebellion, and he indirectly admits as much above. If he's not ready to take on the bulk of the still-rebuilding Empire, what makes anyone think he's able to take on the Dominion with his forces? It's a point that keeps coming up and so many seem to assume that he's the only man in the room who can make it happen and especially after such a candid admission, why is this the case? I'm honestly asking this question out of genuine curiosity, because to me it makes no real sense.
Also, and perhaps more strikingly yet, if and when you meet him in Sovngarde, he's absolutely NOT holding his head high and beating his chest while taking long, masculine swigs of a dead man's drink. Quite the contrary:
Skyrim was betrayed, the blood of her sons spilled in doomed struggle against fate. And so in death, too late, I learn the truth - fed by war, so waxed the power of Alduin, World-Eater - wisdom now useless. By gods' jest in this grim mist together snared, Stormcloak and Imperial, we wander hopeless, waiting for succor.
He's reflective and rather melancholy when he laments the dark folly of warfare the likes of which has so far only succeeded in feeding the great beast Alduin - who is feasting on the souls of his kinsmen. You might have expected him to be overly proud and blustering toward the end, even
past the end in his afterlife. But even he sees the writing on the wall, albeit too late. He acknowledges the loss and even the fact that Nord soldiers of both sides - Stormcloak and Imperial - have found their way to a miserable existence after death in a horrific war. He'll even tell you that "courage is useless" if spoken to additionally.
I imagine that if you got to see Tullius' ghost, he might have similar things to say. After all, that's how I read his actions and his words at the end of the Stormcloak questline, when it's all finished. He laments the obvious victory the Thalmor have scored with the casting of the province into bitter chaos and the subsequent blow to the Empire. Realistically, neither side comes out of the conflict immaculate, even if victorious. And that, again, is what works to make the civil war itself so very tragic. Case in point, even if the policies in Windhelm are of no consequence to you personally, it's pretty hard to maintain that division serves better than efforts at unity in the face of a shared menace like the Thalmor.