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Once you have completed Helseth's quest and received your reward, his quest will not terminate; it will remain active in the background until you reach the required level and reputation with Barenziah to start her quest. However, if you complete Elysana's Robe to Elysana's approval, a message from Helseth pops up saying you should have been faster in delivering his letter, even if you already have delivered the letter for him (presumably he shouts this message back from the dining-hall). Once you get this message, a trigger is started to end Helseth's quest 3 to 7 days later.
You will be approached by a courier after this time has passed, who will give you a note from Helseth along with 100 gold (which may vanish, see notes). If you can manage to get your reputation with Barenziah to the quest minimum within this three to seven days, or Elysana's quest has just added the remaining reputation for Barenziah, her quest will start as usual. However if you don't manage to get the required reputation before the three to seven days have passed, Helseth's quest, which runs in the background will get terminated and you can no longer get Barenziah's quest.
This is a very confusing quest construction which can also lead to a scenario where you can meet two different Lord Castellians at the same time, one for Helseth's quest and one for Elysana's. You can do Elysana's quest parallel to Helseth's quest as long as you don't report back to Elysana once you have delivered the robe. Theoretically you could give the robe and Helseth's letter to any of the two Lord Castellians. For the game they are both one and the same entity, but this hasn't been tested.
In short, the safest way to get Barenziah's quest is to refrain from taking Elysana's quest before Barenziah has summoned you.
Because of an oversight in the questfile, neither the note nor the gold the courier gives you remain in your inventory once he has left. Due to this, players may never discover what the encounter was all about.
The above bugs are fixed by third-party patch DFQFIX, along with many more bugged quests.
I'm pretty convinced that you can also lose the "Baranziah's Book" quest when you do "Painting the Truth". I was waiting for the note to start "Baranziah's Book" but never got it (I reached level 9 after doing "Painting the Truth". I loaded my save of when I started looking for the painting in wayrest and talked to some of the royals. They still had the "Lord Castellian" topic, which according to UESP indicates the Helseth quest is still active and ready to trigger "Baranziah's Book". After I got the painting none of the royals have the "Lord Castellian" topic anymore. I assume I lost the Helseth quest and thus the ability to do "Baranziah's Book". In fairness I did kill quite a few guards/battlemages that came from the main throne room.