Spoiler
You were able to get into the thieves guild. It was difficult to locate; the way you managed to find it the first time was it found you, and offered you an invitation. You took the Grey Fox up on his offer, and after the initiation of steeling a poor old man's diary, you found that the thieves guild was more than just an organization of people that could take requests for merchandise at "special prices" and those skilled at obtaining an item to make it possible for that special price to exist. Your guild master, the Grey Fox, the "King of Thieves" was actually working towards noble causes, mostly protecting the poor for the abuse of the rich. So, as you prove your worth by supplying the Thieves Guild with whatever you could get your hands on, the Doyens and eventually the Grey Fox himself offers you a special job from time to time.
You do things like steel a bust to flush out a rat, get the tax records of the Waterfront, rob a Countess of her ring and give it back to a fence's widow, and break an old friend out of the Skingrad dungeon. And it all leads up to the Grey Fox himself, happily meeting you to tell you that you are the best the guild has, and he needs you to collect a series of random artifacts and items, not telling you what you are after until the end of the run. You are summoned one last time, and told of the Ultimate Heist: an Elder Scroll, from the Imperial Palace Library itself. You muck through a large portion of the Imperial Sewers to get in position, evade several floors of palace guards, outwit the blind priests that manage the library, and make off through half of the palace with the object that will surely mark you as one of the most infamous thieves in all of Cyrodiil. You deliver it to the Grey Fox, and he gives you a wedding ring, where you deliver it to the Countess of Anvil, the Grey Fox revealed that he was the former Count of Anvil, and gives you the Cowl of the Grey Fox, making you the guild master.
You were able to get into the thieves guild. It was difficult to locate; the way you managed to find it the first time was it found you, and offered you an invitation. You took the Grey Fox up on his offer, and after the initiation of steeling a poor old man's diary, you found that the thieves guild was more than just an organization of people that could take requests for merchandise at "special prices" and those skilled at obtaining an item to make it possible for that special price to exist. Your guild master, the Grey Fox, the "King of Thieves" was actually working towards noble causes, mostly protecting the poor for the abuse of the rich. So, as you prove your worth by supplying the Thieves Guild with whatever you could get your hands on, the Doyens and eventually the Grey Fox himself offers you a special job from time to time.
You do things like steel a bust to flush out a rat, get the tax records of the Waterfront, rob a Countess of her ring and give it back to a fence's widow, and break an old friend out of the Skingrad dungeon. And it all leads up to the Grey Fox himself, happily meeting you to tell you that you are the best the guild has, and he needs you to collect a series of random artifacts and items, not telling you what you are after until the end of the run. You are summoned one last time, and told of the Ultimate Heist: an Elder Scroll, from the Imperial Palace Library itself. You muck through a large portion of the Imperial Sewers to get in position, evade several floors of palace guards, outwit the blind priests that manage the library, and make off through half of the palace with the object that will surely mark you as one of the most infamous thieves in all of Cyrodiil. You deliver it to the Grey Fox, and he gives you a wedding ring, where you deliver it to the Countess of Anvil, the Grey Fox revealed that he was the former Count of Anvil, and gives you the Cowl of the Grey Fox, making you the guild master.
And after that? Nothing. You have a piece of light armor that makes the guards ultra-hate you, and makes members of the Thieves Guild love you. There are no more heavily guarded locations that you get to test your skill against and no more special commissions for you to earn a good pile of gold from.
This bothered the hell out of me, and I really don't want to see it happen again.
Here's my suggestion: When you go and finish the guild quest chain, firstly, you DON'T become the guild master, if the guild master has to change its one of his lieutenants, not the guy that was able to raise through the ranks in a matter of days by attending to some of the matters the guild had to face for those few days. It just doesn't feel right that last Thursday, I was just inducted into the guild. and now I'm supposed to be running the whole thing.
Second: How about some randomly generated quests, you make 5 or so locations, you go and talk to your guilds respective handler, and based on an RNG, you are told to go to one of the five locations where a random item spawns and you either have to sneak or fight your way though the location and get the item of value. Then you make your way out of the area and turn in the item. When you exit, the area locks down and you can't get back in until you have another quest dealing with this location. This could work with the Thieves Guild and Mages Guild, as a valuable item or arcane artifact respectively. To add in quests for the Fighters Guild, you could have them play bodyguard or protection duty, where they have to insure that a person or object of high value gets safely to its destination. The Assassins Guild that Skyrim will offer will do the opposite: you need to kill a randomly generated target that will be going to it's destination, and you get a bonus for never being seen/the bodyguards don't find you.
You can also fail these repeatable quests when the object of value is moved to a new location (Thieves and Mages), the person you are supposed to protect dies (Fighters), or the person makes it to his destination (Assassins).
I think this would make guild much more fun. Any thoughts?