Board Thread:Skyrim/@comment-12467746-20130718032552/@comment-11457306-20130719172810

SPOILERS!

You can call me Rider.

Okay, there is a conflict between the two quests. There are 5 small TG jobs for each of 4 of the major holds: Whiterun, Markarth, Windhelm and Solitude. Somewhere along the end of those 4--usually after you have done 3 City Jobs, Tonilia will give you a quest to engage the Khajiit to transport stolen goods. Once all those are done, then you can become guildmaster. BUT if you have killed Vittoria Vicci, then the Solitude City Job will never come up. Without that, you cannot finish the Thieves Guild Questline and become Guildmaster. You must always do the TG Questline first. I ran across this information by accident, but I believe it is in the "Bugs" listing of either the DB or the TG walkthrough on the Wiki.

I am so sorry. I cannot tell you how many times I have told this story. I think I'm going to put it on my blog.