So far I can sum up the Legion quest-line as:
- Intercept a caravan (of 4 guys)
- Intercept a courier (who was killed by a bear by the time I got to him)
- Defend Whiterun from generic, respawning Stormcloaks until an arbitrary number of dead Nord patriots, when I guess they call off the assault.
- And, of course, a half dozen 'attack the fort and kill roughly 40-50 generic Stormcloaks who endlessly respawn until they reach that arbitrary number when the Fort is taken. At least Oblivion gates had a sigil you had to make it to... All the while, I've been getting small payments of gold, and seemingly random-generated rewards.
And then the crowning jewel - the Assault on Windhelm. General Tullius leads seven or eight guys in an attack on the rebel capital, giving a very poorly voiced speech, with a quiver of steel arrows on his back. Firstly, why is the general leading, on foot, like a common grunt? What happened to the regal, stoic, 'Roman-ness'? What general would carry around bow and arrows? Certainly not Tullius, it just looked silly. Worse, the Imperial soldiers were all wearing the light Imperial armor, not the imposing Legion steel - if a general is going to lead a small assault of 'elite' troopers into a rebel city for fierce urban combat, to take a keep, they should definitely be wearing heavy, steel armor. Once again, I fight through dozens of faceless, anonymous, respawning Stormcloak soldiers who remind me of Star Wars Stormtroopers because of their helmets - and they're about as deadly too.
Then we arrive at the keep to find Ulfric, sitting on his throne with his second in command standing in front, threatening me, Tullius, and Rikke who have apparently lost our escort (maybe if they'd been issued adequate armor they'd have survived). I can walk up to Ulfric and talk to him, discussing interesting topics like 'How goes the war?' or 'What does it mean to be Dragonborn'. If I ask him about the first topic he makes no mention of being utterly defeated. Rather, he talks about 'sending a campaign' to take back Winterhold. Anyways, after a brief 3v2 fight we overwhelm Galmar and Ulfrik, the leader of the rebellion is laid low, and asks that he 'be executed by the Dragonborn, because it'll make for a better song' despite the fact that I haven't done anything even remotely Dragon-borny, except for participating in the Dragonslaying at Whiterun. Tullius hands me what he says is his sword, an enchanted Dwarven longsword, to make the kill with. Keep in mind that this whole time, Tullius has been using a generic Imperial sword, so where he got this Dwarf thing is anyone's guess. After I execute Ulfrik, Tullius says 'keep my sword'. Oh great. a Dwarven Sword of Devouring that you'd never even used. How special. Then, we go back outside to give a victory speech to the assembled soldiers (where were you guys when Ulfrik was held up in his keep, and could've had dozens of men lying in wait to ambush General Tullius? Oh and General, you still have that ugly quiver of arrows on your back spoiling your red-and-gold ensemble). This speech was at least a little bit better delivered than the first one, and Tullius admits afterwards that he hates giving speeches. I can see why. But aside from giving me thanks, Tullius mentions that I've done quite a bit, but if I happen to find any remaining rebel camps, make sure to kill them too. Good day, Legate (I've already been promoted to a Legate), see you on the other end of Sovngarde.
- Why do the rewards for these quests need to be random items? In Morrowind, there was Templar Armor, and in Oblivion there was that white armor worn by Adamus Phillida and other high-ranking legion officials - why couldn't Skyrim have progressively provided me with a set of unique-looking, high quality, 'Imperial Legate Armor' or something?
- Why do the quests svck/are so similar? We could've had alot of cool things like being an ambassador to a Jarl on the fence, and your actions to win him over might influence later stages of the campaign. We could've had weeding out traitors. We could've had some 'off the books' missions from Tullius resisting the Thalmor. Instead, we had a bunch of generic Imperial camps followed by a bunch of generic fort attacks.
- Why were there no moral dilemmas, and a shallow story? Alright, I liked the original premise of the Stormcloaks vs. Imperials - I like moral ambiguity. But there's never a point where I need to choose whether or not to disobey orders because it means executing civilians, or stop soldiers from executing prisoners. I never get to see scared Stormcloak civilians who might bring the war to my head, and make me question my choice in who I sided with. All of my enemies wear helmets that mask their faces, making the fight impersonal - I think there are only three 'faces' of my Stormcloak foes where I can look the enemy in the eye.
I think I've come to the conclusion that, if Bethesda is only going to do battles that have a dozen people, it's best to leave them alone altogether. They could've at least had ambient noise of warfare going on, to give the impression that there were other squads of soldiers fighting through different streets of Windhelm that I just couldn't see. The current system where both sides seem to have six or so guys at any one time, and more just spawn through doorways in arcade-like, and frankly beneath Elder Scrolls. In Morrowind, I think that every human NPC (aside from guards and maybe some vampires or slaves) had a name, even bandits. Now they're just Stormtroopers.
I guess all in all the point of post is that I've had a mostly positive impression of Skyrim, but the Imperial quest-line really just jaded me - and I'm almost positive I won't do the Stormcloaks now, as I have no reason to think they'll be any better. I'd expected more from Bethesda. Hopefully they'll take note and, well, do a better job in the coming expansions and a future Elder Scrolls: VI.
/rant

I think a better solution would have been to attack the fort, have the large battle outside, then have everyone head for the doors and sweep out the inside, anything but respawns.