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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.

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    I don't think you get any bounty for the quests if you don't get caught. – Jupotter Jul 31 '12 at 18:40
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    Do note also that you don't have to do hundreds of these jobs - you only have to do a certain amount per city to get the relevant quest - if you get a job for a city you're done with, you can cancel at any point for no penalty. – agent86 Jul 31 '12 at 19:00
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    It's 5 jobs for each of the 5 holds. So you'll have to perform a minimum of 25 jobs, in addition to each hold's "Special Mission" before you get the final quest. – tiddy Jul 31 '12 at 19:12
  • Thank you for the information. I understand I don't necessarily need to do "a hundred" of these quests. But in the end, I might end up doing 50 of them, because I'm not keeping track of what I've already done. – theJollySin Jul 31 '12 at 20:37
  • Also, the Elderscrolls wiki and the UESP wiki seem to disagree on this. Do I only need to do the Delvin quests to become Guild Master, or do I need to do the Vex quests as well. (I have been doing both for the money, anyway.) – theJollySin Jul 31 '12 at 20:39
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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.

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