The most notable change I noticed with the Thieves Guild actually occurred from Daggerfall to Morrowind. The ones in Daggerfall were much like the organized crime today - they were a syndicate of thieves tasked with not only doing contract work for clients, but they also tried to keep the city's criminal underworld under their control and eliminated any freelance thieves and mercenaries who weren't associated with the guild. It was basically an incredibly badass gang of mobsters: it wasn't until Morrowind when they started to get that "ragtag" feel everybody is describing. :rolleyes:
I can't quite remember all the quests from Morrowind, but unless I'm completely mistaken, they were a pretty badass gang of mobsters there. Only Gentleman Jim Stacey and his Bal Molagmer quests were really Robin Hood style, and you can even choose not to do them if you're not that kind of guy (I specifically remember Jim telling me something like that). Before that, you did actually execute freelancers, you did hire muscle for your base of operations, and you did fight over territory with another criminal organization.
I think you're thinking of the quests involving the Cammona Tong as Robin Hood style. But they only seem like that because the Cammona Tong are racist and not very likable. Other than that, they're no different than the Thieves Guild, and the whole thing is really nothing more but a war on territory.
Anyway. What I didn't like about Oblivion's questline was that it was too personal. The Thieves Guild were simply the lackeys of the Gray Fox, and they were as loyal as any knightly order could have been to their king. But the Gray Fox, he was noone who was worth fighting for. He didn't have a masterplan for the guild. In the end, not only didn't he have a masterplan for the guild, his only masterplan was actually to
leave the guild. The Thieves Guild was portrayed as if all they were looking for was the next cool heist, when it should really have been important what comes
out of the heist - a whole lot of money, for instance.
At some point, I just really wanted to start a rebellion.
What they should have done was to set it up like the Barksdale organization in The Wire... have the Gray Fox as that mystical man that everyone's longing to get a look at, while Armand Christophe actually seems to be in charge, and is handling the "business". Yes, that should have involved drugs too. There should have been a lot more mistrust, tension, struggle for power. And at the end, when it turns out that the Gray Fox's "big plan" was to steal a bunch of things that have
absolutely no street value, completely for his personal gain of being able to get his identity back (while also endangering the Guild with these high-profile heists)... the Guild should have gotten rid of him, and set up a new order.
There are a lot of concepts I can understand in the Thieves Guild in Oblivion. For example, the "no murders" policy. It makes sense because of business reasons. We never hear those, sadly. It would have been so much more awesome if Armande Christophe had lectured us in how murders cost bribe money, and stuff like that. (Seriously guys, watch The Wire to see what I'm talking about here, all the Stringer Bell dialogues are basically how it should have been..)