Hi ! This thread is for those of you who have experienced characters in the DB and Thieves Guild.

My characters have always been the hero types so they do the MQ, Dawnguard, and Dragonborn quests. I tried to create my second character once, Ariadne, to be an assassin... she was really good at it but she had to quit because in almost every town she entered a bunch of thugs were ready to kill her, she had a lot of bounties on my head, she still has these bounties in her inventory. So I had her join the Dawnguard and so far she is happy being in it.

But I'm still interested in creating a character to join the Thieves guild and make another try at the DB. Please share with me the life of being these characters, will they always be in hiding? Will they always have bounties on their heads? Will the guilds make them less free? Aside from the material rewards that they get from killing others and the trophies of the stolen goods, what other rewards are there in store for them? My "hero" characters get unique items from the quests plus the reward of knowing that they have done a good deed. Are the assassin and thieves guild for evil characters? Evil, meaning stealing from or killing innocent people ( example, I think Grolad is not innocent, she deserved to die). Thanks so much for your advice!

The way I see it, hiding is what assassins and thieves do. They would not want to pull a job out in the open where everybody will see them. It wouldn't make much sense. So yes, they will almost always be in hiding. I think it comes with the territory.

None of my thieves or assassins have ever had a bounty. It's a matter of professional pride to them that they never get caught.

I am one of the few who actually like the Thieves Guild and Dark Brotherhood quests, apparently. I like them better than the quests in Oblivion. I like the NPCs, I like the atmosphere of the Ratway and the Sanctuaries, I like the stories the quest lines tell. And I like playing sneaky characters once in awhile. It's a great change from the warrior-type characters I usually play.

I don't feel that the guilds make them less free. The way I see it, the guild quests give their adventures a bit of structure. They are free to kill or steal on their own, as freelancers, if they so choose. Some of my characters do leave the guild, in fact. I make this part of their story. others are happy to be a part of an organization. It all depends on the character.

Assassins don't need to be evil. Pick your targets as you will, either good, bad, or rich or however you want to pick them. You might get bounties but for me the pride of being an assassin is not the recognition or the good deeds. It's being able to get in, kill, and get out regardless of what's in my way. Of course it's also fun to play an evil assassin where the fun is murdering everything everywhere. You don't get bounties if you aren't caught, usually, and you can't get caught if there's no one to catch you >)

Oh and you'll get unique items as well and the reward of knowing that you can kill the strongest, most noble hero out there while he's shining his armor.

Definitely practice your sneak skill and use that along with potions of invisibility to avoid the bounties. Thieves Guild questline has more unique reward type items, including a really cool sword; but in my opinion DB has a more epic questline. (I liked DB in Skyrim over DB in Oblivion, but I preferred Oblivion's TG questline to Skyrim's).

If you get a bounty, you can pay it off or serve time in jail. Once in jail, you can alternately escape, but your bounty will remain. If you are in the Thieves Guild, there is a dialog option to pay a lower bounty. But, it's best just to not get caught, so there is no bounty.

You may want to think about more unusual character stories/roleplay if you have trouble playing a dark character. I'm planning a Mountebank / charlatan / snake oil salesman / travelling juggler kind of character right now, for example- humorous rather than sinister.