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So I know where it is located and how to obtain the key.

There are three potential encounters with their representatives (four if you count Attile) before joining:
Nagur, Halvor and Rengaru.

So my question is can I send 2 of them behind bars for 100 gold each and still be able to join? I'm asking because I really want to complete my quest for Baltram, hang Nagur and get to the Thieves Guild for more quests. Also Baltram sells 10 apples which are extremely juicy and I just love apples in Gothic series.
This question / problem has been solved by helpo1image
You can join them even if you send all of them behind bars.

Basically, if you let all three go, they'll invite you to join them. You can go there peacefully and they won't want (that much) money for training.

If you snitch on any of them (one, two or all three), they'll send Attila to assassinate you. If you overpower him, you can get the key and go to the sewers. Jesper will be surprised, but Cassia will still give you a chance to join them, although they'll obviously be less friendly and will require (more) money for training.

To be exact, Ramirez will require 150/300 gold and Cassia and Jesper will teach for free/100 gold.
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helpo1: You can join them even if you send all of them behind bars.

Basically, if you let all three go, they'll invite you to join them. You can go there peacefully and they won't want (that much) money for training.

If you snitch on any of them (one, two or all three), they'll send Attila to assassinate you. If you overpower him, you can get the key and go to the sewers. Jesper will be surprised, but Cassia will still give you a chance to join them, although they'll obviously be less friendly and will require (more) money for training.

To be exact, Ramirez will require 150/300 gold and Cassia and Jesper will teach for free/100 gold.
Well, I sent behind bars Rengaru and Nagur and it costs me exactly 300 gold (Ramirez) and 100 gold (Cassia/Jester), thanks!