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Are there any workarounds you can think of in game, or maybe a realistic reason to ♥♥♥♥ over a mate and abandon morals?
OP must be mixing up Madesi and Talen-Jei, both have quests involving rings and are both Argonioan, easy mistake. But you blackmail Keerava not Talen but he still takes a disposition hit and when you have done his quest it is a bit weird, he greets you as a friend and tells you to leave at the same time.
@OP Thieves Guild for good guys is the best option, even if you get a new computer you can just install it again. It makes enough sense in-game you are joining the Thieves Guild, you are not Robin Hood, you are a criminal. At that point you are not actually in the guild yet, it is another test, and unlike the previous one you can not fail.
That guild feels like it kills the game I dont know. Dont like them at all.
wat
But, but, but .... I WAAAAANT to be a good guy and not miss out on any quest rewards! 😭
Milk drinkers. Ugh!
But Skyrim's Thieves Guild is closer to an actual gang of b*tch-@$$ hood thugs, and deserve to be slaughtered. Use the Configuration power to disable the Odhaviing requirement so you can get the letter implicating Maven in a murder plot against Mjoll, and you can let Mjoll kill her.
If you do it just right, you can command Jenassa to kill Brynjolf to get things started, which will aggro Sapphire and Maul, and they will get killed early as well.
You can still get the skeleton key and be a Nightingale, if that's what you're into. And you can still do the Stones of Barenziah, as well as buy Dark Brotherhood stuff from Delvin's ghost.
If you want to get the rewards, then you have to get a bit grubby.... At least it's not the Dark Brotherhood, where you have to kill people for money to get the rewards.... Until some "Genius" yes the quote marks are indicating irony.... and? decides to do a Dark Brotherhood for good guys mod.
Sadly, that mod already exists, although it's my understanding that it's more of a "let's make the targets villains so you don't feel so bad about killing them" thing.
The Thieves Guild is an honorable organization. They keep the crimes of the rich people in Riftin at bay.
They target rich people because rich people have the stuff worth stealing, they don't target the poor because the poor have very little worth stealing. Given to join them you have to FRAME an innocent vendor, it's safe to conclude that honour doesn't enter into the equation.