So, in my first playthrough, I went and basically said '[censored] both sides, I'm staying out of this', but I was more sympathetic to the Empire's plight than the Stormcloaks.

However, this playthrough, I'm wanting to pick a side, and am leaning towards Empire, but I don't know. Stormcloaks sound nice at first, but Ulfric seems to be more about rabble rousing, using Talos worship being banned as a false platform for his agenda, and most stormcloaks I meet are jerk asses. Then the Empire, no longer the cool guys with a spine I knew in Oblivion, are fearful of the Thalmor, which is understandable seeing as they pretty much bent over for the elves, but still. I want to help the empire in some ways, but I pretty much hate both sides and feel like Balgruuf, siding with Skyrim, not playing sides.

Well, maybe you should try out what fits best for your character.
If you are a roleplayer, you could take a look at you background to see which side would make most sense.

Well, I'm starting to tip back to thieving despite intending a more honourable character, because there's no money in being a sellsword than thieving. My characters are always a 'profiteer/smooth talker' type.

I'm with the Empire, now and forever, through thick and thin.

But here's why I do so in Skyrim:

- They're trying to maintain peace as best they can (granted they haven't done the best job, but Stormcloaks certainly aren't helping), and the Stormcloaks are doing nothing but putting a thorn in their path.
- If there's any hope of overthrowing the Thalmor, it's through a united Empire, not separate provinces.
- The empires goal is to shut the Stormcloaks up so they can get back to dealing with the real enemy; the Thalmor.
- Stormcloaks are mostly just foolhardy, overemotional Nords who have been tricked into following Ulfric because of their Talos worship.
- Ulfic just wants to be king, and is using dissatisfied Nords to meet his own personal ends.
- Empire is more powerful.
- My character is an Imperial, so they're the natural choice.
- Imperials are hostile in the beginning where you're mistaken for a prisoner. That's about it. Stormcloaks are mean pretty much all the time. Especially in Windhelm.
- Stormcloaks are racists.

Gotta decide what your character would do. If you want OOC knowledge of events.

http://www.imperial-library.info/content/great-war - Brief history of empire since 4e1 and Events and aftermath of the great war
http://www.imperial-library.info/content/rising-threat - Thalmor modus operandi
http://www.imperial-library.info/content/ciceros-journal - A bit of info on current events in Cyrodiil come Skyrim's time.

The rest you're going to have to get from folks in the game. Talk to people and judge them for yourself I suppose.


Just a heads up though, a sellsword would probably fit in better with the empire. The stormcloak recruiter explicitly says they don't want sellswords.

Ehh, my character last time wasn't really a sellsword, being a merc is boring to RP, Im always a thief to some extent. Last time, it didnt matter who was who. I played just friendly enough so I could steal their goods without being noticed, then sit back and profit off their valuables. My characters, which are really just extensions of myself, dont care for the politics, they like the easy living being a skilled 'gentleman thief' brings.

Well, maybe the Empire would make most sense then, coming from a pro stormcloak like me.
The Empire has more wealth, which your character could make profit of when ranking up.

The Empire will put Maven BlackBriar in charge of Riften if they win, so that is one reason for a thief to join the Imps.

Plus, like ferrykeizer said, the Empire probably has more money to throw around.

There is no right and wrong, both sides are grey, have their upsides and downsides. this was obviously intended to stop people saying " im choosing them because they're good guys."
It means you have to think about your choice, and the way it will impact the world/lore. basically either choose the one you prefer, or go with the roleplaying option and choose which side you think your character would choose.