I rolled up a rogue yesterday in order to experience the game as a silent killer. I have a tank-like character before this, so I thought I'd try the game as a roguish Dragonborn who is no less honourable than my Harbinger; main difference being that he kills quickly and silently, unlike my warrior who charges into the fray with sword raised.
My question is this:
Are there missions that send you to an enemy behind the lines to sabotage their efforts, mislead them, assassinate high-ranking commanders (maybe not that honourable, but an effective war tactic nonetheless) etc? I know that joining the Imperials would involve some of these missions, but besieging a fortified objective as part of an army in a frontal assault isn't my rogue's cup of tea. So, are there any factions that also give out clandestine missions that also help win the civil war and solve other troubles afflicting the land?
I've joined the Thief's Guild, but many of their jobs are about preying on innocent people and extorting their hard-earn gold. The Dark Brotherhood is a no-go either, as killing innocent people for money is abhorrent to my Dragonborn.
Do I have to join the Companions, like my warrior, to make a decent living? I like that they rescue kidnapped citizens, kill violent criminals, and protect villagers from wild animals.
Playing a James Bond type is hard... but I thought I'd point out a couple of things here:
1st: There are the Civil War quest lines (Stormcloak/Empire Factions) - they can all be performed by the sneaky/stealthy character and both quest chains provide a story where you as an independent auxiliary are required to use your unique skills ( securing the crown was interesting as a stealth type).
2nd: Your use of stealth really is a game-style decision... my DB assassin character used stealth even in non-stealth situations, such as the fort fights, to infiltrate and create mayhem behind lines... while the main-line troops were fighting in the courtyard, I found the keeps/prisons to liberate what i could before the battle ended,,,, indeed in one mission you have to sneak behind enemy lines to free prisoners... this sounds like exactly what you were looking for ...
3rd: specific missions in these chains you can use your stealthy stuff exclusively ... intercepting a courier, or ambushing a weapons convoy, or infiltrating and using blackmail to get info ... all these things I found...
Basically, I found that these different quest-chains have a different feel to them, based on the character and play-style I chose to use.