On deciding which faction to side with on this playthrough, I'll input down my previous characters' choices:
None of my main characters have gone 50+ yet. I'm hoping my 4th one will make it though.

1st=Empire (completed)
2nd=Stormcloak (30% then my save files went hoo-hoo)
3rd=Stormcloak (70%)
4=?

Okay so this time around my I think I'm feeling what my char is feeling so I'll input how the story went:

So my 1st character was a hardy male Nord who loved gourds, the 2nd one was a lover of my first one and was a female Imperial, the 3rd one was the alter ego of my 1st one which now loved the arcane arts, a male Altmer, the 4th one was the product of wanting a bit of everything, a Breton,

Now my Breton was on her way to the Palace of kings in Windhelm to join the rebellion (but not before emerging victorious on the "Blood on the ice" quest) and taking the very same and epic footsteps my 2nd and 3rd character when they were about to knock on the palace door.

Once inside the palace and staring peacefully at how the sunlight gleams upon Ulfric's eyebrows, she approaches him slowly and hears his "voice" as it gets clearer and nostalgic she initializes the "Dialogue", still her mind lost in thought of the bliss of being able to once again retry to complete the Stormcloak rebellion questline that her other two predecessors have failed at, she glances around the palace and smiles..

As she waits for Ulfric's voice and dialogue to finish, her eyes passes by his forehead again and sees the sunlight gleaming down his eyebrows, then she looks down, she sees his eyes for what seems like the first time.. In those moments she "SAW IT", her face now horrid of dread staring into Ulfric's eyes and her mind flashbacks to the her previous predecessor's history and experinces from their beginning in helgen and now present, she saw it again Ulfric's eyes

... She ran outside as fast as she could and fast traveled to Whiterun, picked up Lydia and headed to Solitude to join the Legion...

Ahh, seeing Tulius again whatta relief she thought. She waits for Tulius' speech to finish (Lydia gives a yawn) then Tulius proceeds with his intended plans.. Then she suddenly recalls again at how utterly booring and bland the Legion questline is, and decides to the local tavern for a drink.. Now she's at a crossroad...

So any suggestions on who she should side with?... Thanks.

... Again? You know how this thread is going to go once Colonel gets wind if it. Or any if the usual suspects. Within the next hour we'll be discussing which sides uses what condiment when they eat babies and the moral implications of Siracha vs. Tabasco.

They should just have a civil war subsection.

Right now, it's the same old back and forth speculation and theories on both sides, nothing has changed.

I've never actually played the civil war because I've read that the game doesn't handle the aftermath well. Whiterun never cleans up. Characters continue to talk as if the war still rages and Ulfric still lives, etc. So, I've always chosen to leave it as a backdrop feature of the setting, with my only input being to negotiate the best possible result for the empire during the main quest.

In fact, I really hate that part of the main quest because it doesn't make sense ... why do you have to negotiate an exchange of unrelated territories just to obtain a temporary cease fire at Whiterun?

I choose to side with nobody, at least in any formal capacity. But, if you are wanting to take a side and don't really have a preference then why not take the side you haven't completed yet?

Pfft clearly the empire uses the superior condiment, mustard and the stormcloaks settle for bland and boring ketchup

Why did that make me want a hot dog?

You should join the elusive Ass Bandits.

Aren't our chars somewhat all in that faction? They all just turn out to be kleptomaniacs anyways..

You're forgetting I'm always defending, not bashing the other side.

As I am keenly reminded every day, of every week, that this painful discussion reoccurs like some sort of demented Groundhogs Day loop.

I didn't even read the thread and I vote Empire.

Not much better to discuss as of late.

If you mean defending by means of repeatingly "staggering with your shield" then no.

Plus a 4-year long debate in which we find who started the Vigilants of Stendarr and if it's worth it to build a time machine in order to prevent it's founding.

When I started seeing a thread about the height of an NPC, I already came to the conclusion that we're at the bottom of the barrel. Not even that top of the bottom...We've kicked the barrel over, and we're scraping the dirty, moldy, pill-bug ridden underside...
...Because we're bored...And arguing Empire vs Stormcloak is easy fruit.

Well my current character is actually looking at it from a different perspective for me. She's a Nord, from Bruma who's parents fought in the Great War for the Empire. She went to Skyrim to help stop the rebels and get the Empire back on track. She's visited several cities and have done quests both Stormcloak and Empire related. In the end she has come to just one conclusion. The war must end. It doesn't really matter anymore who wins, it just has to end. The suffering on both sides will never stop until the war is over. So, she will be joining the Empire in stamping out the rebels. Not that she doesn't somewhat agree with the rebels or see their side of the conflict, but that just doesn't matter nearly as much as just ending the war, period. And that's what she intends to do.