Yeah I'm a kinda OCD roleplayer, I actually deleted my thief to start over once I realized how he definitely wouldn't have sold his soul for the dubious honour of guarding some insubstantial thing like a concept, it's certainly not the sanctuary which gets attacked (and why would anyone bother attacking it?)

The whole thing was executed a bit badly imo, there was never any incentive to really become a Nightingale other than to continue the story and become the guild leader, which is what I wanted so I could bring the guild back to glory. Even the nightingale armour is given to you before you sign your soul away, you can just run off and take it. If looking like Batman in a medieval fantasy game is your thing.

I found that Skyrim in general forces the player to go against his character's nature, in order to do things the player wants to do, here's a list of the stuff I found so far.

You have to become the Dragonborn (officially recognized as such) to complete the Imperial storyline. (probably Stormcloak too)

You have to join the College of Winterhold to complete the main story.

You have to join the thieves guild to complete the main story, unless you want to stack up enough stuff to pass an 80% speech check.

You have to become a werewolf to complete the companion storyline.

You have to become a nightingale to complete the thieves guild storyline.

You do for the Stormcloaks too, which annoyed me, since I wanted to finish that line before I started the main quest.

Also, not gonna lie, I've been using console commands to get myself into the college of Winterhold without officially joining it. Just type in TCL and fly in there. It's a few seconds of cheating, but it makes up for not having to be associated with the college for the rest of the game.

Yep I think this kind of thing is basically handholding, like assuming if the player hasn't joined the thieves/mages/gotten shouts yet etc, he must just be a really bad player, and will need to be violently steered in the direction of "playing properly"

Epilogue: So I played the questline through to the end, returning the Skeleton Key to Nocturnal and becoming an Agent and so forth.

By the time I got to the end after actually spending some time in the Twilight Sepulchre, I felt a lot better about the "deal" with her. At first I was horrified when I heard about the Nightingale Sentinels who had gone crazy after being cooped up too long guarding this place. But when you ask Gallus, Hey, where is everybody, he's like, Oh, most of them don't work here any more, a lot of them took off. And Gallus himself is released from the Sepulchre for his long years of good service once you return the Key. Plus there is a lot of talk between Point A and Point B about how you'll have to work for Nocturnal "until your contract is fulfilled". So overall it sounds way less like the eternal bondage I was worried about and more like a (relatively) short-term agreement. I'm cool with a few centuries of an easy night watchman job in exchange for several decades of cool shadow powers, good luck, and Nocturnal's friendship now.

If I remember when you return the key she says you have paid your end of the bargain, so the whole forcing you to play guard for eternity doesn't have to happen, but still it is bloody annoying and entirely out of character for me, especially given that I only joined the Thieves Guild with the hope of taking them down, as well of course for seeing the storyline >.>; At least the DB has a quest in game to destroy them. (Modders please save me here!) Either way the fact that it railroads you into bargaining with her is very stupid.

Yeah. I was thankfully able to work it out in my case, but it's too narrow a path, RP-wise.

I have yet to understand what the frack those nightingales are. You get no powers after you pledge your soul to nocturnal (yea you need to first kill the traitor....so erm why pledge first and not go kill him with that shiny armor), second you are still a thief... like you need all that bad ass armor just to rob people, draining life as a thief? really?

It would be nice if after killing the traitor you would get an option to either join nightingales and leave your thief past behind and become vigilanty or refuse the gift, keep the key and be somehow haunted//hunted by other nightingales.

Why do you expect? This is the least robust TES in its history. May as well be Redguard 2.

My disk is already back in the box waiting to get traded back into Gamestop.

It is definitely confusing. Really the armor doesn't seem to have anything to do with it; it's just traditional to wear it when talking to Nocturnal I guess.

I also thought it was insane that Karliah made the pledge on my behalf. All I did was go stand on a rock while they pvssyd.

And everything Gallus said seemed to contradict half the stuff that Karliah said.

I also kind of wanted to know more about the actual Nocturnal priests, the ones that the Nightingales said were just weird and not to be taken seriously. Can I talk to one of these guys?

All in all, it was a real mess. But when I finally got to talk to Nocturnal herself, I was happy with what I heard.