I have never done a single quest in the Civil War. I have seen some let's play videos on it and I am not interested in it. I might give it a try when the enhanced version of the game is released. I itching to play7 the enhanced edition since it is still very hot where I live and I can not stand heat higher than 15 Centigrade or 59 Fahrenheit. Yes I hate summer.
I haven't done the Civil War since November, 2011. I can't remember what I did in regards to Holds or what towns I took back. All I remember now is that my character sided with the Stormcloaks. I've been meaning to do the Civil War a second time so that I can side with the Empire but I haven't been able to bring myself to do it yet.
The only time I did season unending I swapped Markarth with Riften (That is all I can remember). Most other times I just sided with the Imperials - except once I sided with the stormcloaks - then didn't like the post-ending - So I reloaded and sided with the imperials again.
Thought the Stormcloaks were too prejudiced.
Most recent playthrough - used the timing is everything mod and ignored the civil war entirely - Decided the civil war is too big for one character to determine the outcome on their own.
None of my characters have ever done "Season Unending" as they won the Civil War for the Empire and rendered that quest moot. The main thing my character's give Ulfric is the business end of their weapon at the end of the Civil War.
The Civil war questline was not good.
It is more of a chore, than a fun part of the game. I feel like Bethesda puts out their base games, then lets the Modders fix and finish them. A lot of Skyrim feels unfinished, like something was going to be put there or in a spot, but they just didnt finish it.
That is the good and the bad of the community. Bethesda knows the Modders will fix their games, and add to them, making them much better than at production.
I rarely do Season Unending. When I do, I generally remain impartial and give each side what I consider fair compensation, unless I'm playing a completely biased jerk who's willing to abuse his/her authority as the Dragonborn. Most of the time though, I throw negotiations out the window and simply kick the crap out of the opposing side before starting The Fallen. It's more fun that way IMO and meeting Ulfirc again in Sovngarde when I join the Legion is a really nice touch.
I side with the Empire, but hold off on resolving the civil war quest so I can do Season Unending, where I hand Markarth over to the Stormcloaks as part of the negotiations to discreetly dispose of Ondolemar- and when I retake it, I'll have completely removed the Silver-Blood family from Markarth (as by then I'll have killed Thonar).
After killing Alduin and finishing the civil war, I plan on using one glitch or another to get back into the Thalmor Embassy afterwards so I can kill a now-nonessential Elenwen.