So how easy would the Thieves Guild be?
I would say that difficulty depends on which difficulty you selected, because there are several Theves Guild quests with multiple enemies and stealth is pretty difficult to achieve. Personally, the theves guild was the most boring quests to me. I know theves are supposed to behave like criminals, but the characters are so anoying, it makes me want to exterminate every soul in the Rataways. Especially the guy who keeps saying he's going to smash my face in. He's really got a death wish. I might just give Lydia the green light next time I'm down there.