Hi. So, I believe I completed the Thieves' Guild main story (met Nocturnal and became a Nightingale and everything). However, I don't seem to be the new guildmaster yet, which I believe is possible? The UESP is rather unclear on this. It says something about doing a certain number of extra "jobs" for Delvin and Vex, which I have done for quite a while now. Nothing new. Do I have to complete all kinds of jobs at least once or what? For instance, I can't do jobs where I have to pickpocket people, since I never leveled my Pickpocket skill and it's still on 20 or so, so they always notice me.

Or did I miss something? Any help will be appreciated.

You have to complete 5 jobs in every major hold besides Riften.

That's 5 in Solitude, 5 in Markarth, 5 in Whiterun, and 5 in Windhelm for a total of 20. Type doesn't matter. I only do the heist and numbers jobs.

After doing 5 in the same city Delvin will give you a special assignment. Complete that to increase the Guild's influence in the city.

After you do all the jobs, return to the Cistern and become Guildmaster.

you'll know you did enough in each city when Delvin gives you a "special" task that usually ends with you now having access to a fencer in that city to sell stolen goods to. Saves you having to head back to Riftin every time.

Each time you complete one of the requirements for a city, a merchant will fill a stall in the Ragged Flagen. Once all stalls are full, you'll be invited to a special ceremony. Its pretty cool.

But man do you feel like you grind out a lot of thieves quests.

I wonder if you can do them all before Nightingale quest takes place.

I did all of them before doing the Honey estate so yes, you can do them before nightingale which makes you being the guildmaster seem much more worth it.

Sweet cause I think i'll do the same then.