The game plays better if you pick a side in the war as early on as possible? I ask this because I didn't pick a side until I completed the main quest with a character that had over 300 hours logged. I thought it was a little silly that both ulfric and general t. gave me zero respect ( considering all that my character has done for both them and skyrim) when I finally decided to pick a side. Does the game flow a little more realistically if you side up early on? Might make joining my first priority next go around.

If you want to do the Civil War before the Main Quest, I strongly advise you to complete the civil war quest storyline before attempting the main quest. There are known issues with quests when you're sort of part of the way through both storylines, or trying to do both at the same time. There's a lot of overlap between the civil war and the main quest, and so people get strange glitches or are otherwise "stuck" with broken quests, quest objectives not progressing, etc.

That being said, I can't comment on how the game flows if you do Civil War and then Main Quest, since I've only ever done them in the reverse order, or had characters do one but not the other.

I moved your thread. Rule of thumb, if you have to put (spoilers) as a caution in your thread title, it should just be in the spoilers section.

As for topic... I dunno - I have a couple hundred hours in and just don't feel motivated to pick either side on either my dunmer or my bosmer, because I can't come up with a reason why either of them would care. I may roll a Nord or an Imperial and purposely play the Civil War quests.

I really don't think it matters. Everyone (and I mean EVERYONE) treats you like crap regardless of who you are. You can be the Thane of all the major cities, at the top of all guilds, the Dragonborn, champion of the Civil War, and slayer of Alduin and everyone treats you like garbage.

Can we become Thane of Windhelm without doing the Civil War? I think I've read in other threads that we can't. On my current (1st so far) character I completed the Civil War so I'm Thane of Eastmarch (I think that's the 'Windhelm' title) - I just happen to have put it off - but I think I've read that we have to complete the Civil War before becoming Thane in Windhelm.

Good question - I would like to know this too, since I have little interest in the civil war (unless I get to take out more Thalmor), but I really would love to have the house in Windhelm