I wanted to do this for a long time. Much like a Robin Hood type of character.

I pretty much like the idea of a sneaky fighter who uses a bow to put an end to her opponents quickly, and a blade in those common moments where she decides to just run into a group and spill some blood. Maybe even illusion?

The problem is that you have to be a thief if you want to become a Nightingale. It is not too much of a big deal, because my character could start out like a poor woman who joined the guild out of despair. So eventually she feels sorry and stops aiding the guild. However, Riften will still hate her.

I can always refuse to become a guild master, no problem. And ofcourse steal from the snobby rich ones to give it to the poor. And ofcourse aiding the Jarls and the people.

However, other than that I can not think of ways to be a good moraled Nightingale, do you have any ideas?

I dont think its possible since the nightingales are Nocturnal's [censored]es.

maybe avoid becoming a nightengale, but otherwise it can work with enough imagination, it's not outside the realm of possibility

Nocturnal seems to be more focused on shadows and mystery instead of truly evil matters. So I do not see any problem in that. Shadows, mystery and darkness are neutral IMO.

I want her to be one, it is part of the story.

A nightingale has to serve nocturnal in death.

I know. I don't mind that my character will go to her after death.

^

you'd be selling your soul to a daedra

No problem for me. I actually want that, it gives a dark though not evil touch to my good moraled Nightingale. Like Vampirism, you can be one but you do not have to be evil.

oh.

I think your character and Karliah will get along fine.

Yeah I think so aswell. It is not that my character will break the oath of the Nightingales when she is doing good deeds.

I don't see a major problem with this roleplay idea. The oath to Nocturnal is a business transaction, not a religious vow. And as far as I know Nocturnal doesn't care what a Nightingale does with stolen loot. So I think you could roleplay a Nightingale who abandons the Thieves Guild, steals from the rich and gives it to the poor, all the while staying in good graces with Nocturnal.

Well, the previous two games have had robin-hood style theives (In morrowind, the guild master was this, and the whole guild in oblivion was robin-hoody) so it's feasible; and Daedra or not good or evil.

You could also avoid killing people where possible. Instead slink past unnoticed or distract them with arrows so you can pass by whilst they investigate, etc. If you're aim is to steal from the rich to give to the poor, theres no need to bring violence into it if at all possible.

Once you go Illusion, you can't go back.

I mean seriously... Once you have tasted the power to turn entire towns on each other; you would only want to be more powerful. Then you would go Conjuration and send Daedras to chase people around for you amusemant... Then you would turn into a vampire to give your Illusion spell an extra "oomph"... Then the next thing you know, you would go around biting people in the neck and turn them into chickens.

I do like illusion, I'll probably add it to my skill list.

Let's see what I got anyway:

One-handed

Archery

Sneak

Illusion

Blocking

Light Armor

Maybe pickpocketing and speech?

Because of the legendary feature, it shouldn't be a big deal if I got a bit more skills than needed. But perhaps I might abandon archery and stick to the idea of an agile swordfighter.

Pickpocketing and speech may or may not be needed. Pickpocketing to steal from the rich, but to reverse pickpocket some stuff for the poor aswell. Speech could be nice in cases I want to play a merchant, or for persuasion.

Bringing violence to bandits and other threats to the people are fair for me.

But killing those snobby rich bootlickers? Naaaaah.

And in no way would my Nightingale harm the innocent ones.

I'm warning you! I once went down the same uptight, self-righteous road as you (no offense), but ended specializing in magic and sneak because I just cannot pass up the sheer hilarity of luring Mammoths into towns!