Wow. So all of that was on the Stormcloak side, too? Because they have you do all of that stuff on the Imperial side as well. :/
I have a theory about the Civil War quest line. I think it was initially concieved of as part of the main quest, and at some point in that quest we'd decide to pick a side and fight for them, or force a truce. As the game developed it was splintered off into a stand-alone quest line, but there wasn't enough time to flesh out both sides, or make the war more compelling. Thus the duplication of the quests on both sides and the general haphazard feel to it.
I have nothing to base that on other than the game itself. Starting a second character made me realize how deeply the civil war story is tied into the start of the game, which is odd - the're basically framing the entire introduction around a side quest. My understanding is the Civil War touches part of the main quest at one point, which may be an artifact of how they once were connected.
I know Skyrim is all about player choice, but I kind of wish the game would force you to slow down, do a certain number of quests, then allow you to proceed. This would allow the world time to react to the events unfolding in the war.
This is the blessing and curse of this kind of game: you can go at your own pace. But the world has to accomodate it. With rare exception, you're free to walk away from events in progress, and when you come back, they are still in progress. If you want to tear through a quest line quickly, you can leverage fast travel and focus on it and do so quickly. Or you can draw it out as you see fit, and everyone involved will let you.
There's a quest for the Dark Brotherhood that highlights this dilemma well. At one point, you have to kill someone at a wedding. Because the game allows us to pick and choose our quests, we are not forced to go straight there and kill them. The downside is, that wedding will take place every day, forever, until we show up and kill them. They're just there so we can kill them.
It's what I've taken to calling the World on Pause feature. Basically every important thing in the world waits for you to come along and influence it directly, without forcing you to do so. To make a believable world, there are all these game systems to create the artifice of a living place, things happening. But really, everyone is going through motions waiting for us to come along. That's the primary source of tension in the games I've played (Oblivion, Fallout 3, Skyrim).
A compromise system would be for Bethesda to work in more consequence (ala the Civil War quest line), but also partial failures if we dawdle too long. Imagine if we had a goal to kill that person at the wedding, and we got a bonus if we did it during the ceremony. But if we don't, and miss the ceremony, we still need to kill them where they live, we just miss the bonus. Of course, as soon as that kind of timed event is introduced and expanded across the game, the complexity of the game just detonates, and it's already an incredibly complex game to build.
Personally, I wouldn't have it any other way than it is now. I relish the freedom to take my own pace, and walk away from quest lines when I feel like it, returning when the mood or convenience fits. But letting me do so means there are some peculiarities that must exist.
