I admit, I like stealing things. (In-Game, of course.)
I have a classic assassin rogue, and I felt like joining the Thieves Guild was the way to go. I finished the Nightingales quest line and am close to being the leader of the Thieves Guild. But I am starting to get a little concerned about what I need to do to make it all the way.
If I do ~100 of these Thieves Guild radiant quests from Delvin and Vex, will I end up with huge bounties in all the major towns?
I just refuse to go to jail. It's worse than losing the game; I'm not going to do it.
Best Answer
As long as you commit the crime while undetected, you'll not accrue any bounties. Numbers and Heist jobs are particularly easy in this regard, as often times you can show up after hours when nobody is around. In many cases, these jobs take you to places where nobody goes - there's pretty much no risk of being caught for many of the ledgers/strongboxes.
I tend to save beforehand so that I can reload if I end up getting caught, but with a high enough sneak skill, you shouldn't have to worry. As long as the "eye" is completely closed when you interact with the ledger/strongbox, you're good to go.