I think that Random quests could be a huge improvement for guilds if done right. Here's what I think should happen.

When you join a guild you have to have certain skill requirements to get higher before you can advance in rank and continue the story of the guild. To help you do so is randomly generated quests between the main story quests. These can also be done at any time for other rewards such as armor, weapons, or money. After The guild's story quest is done you can continue to do random quests, I hated that there wasn't much to do with finished guilds in Oblivion.

in the GI article it said Radiant Story would choose locations for your quests based on previous expiriences, so I'm guessing slightly random quests could be implemented. But it would be awefull hard to create a game-guide for something like that...

or rather than one guildmaster giving out all quests..

have the guildmaster give out the main quests.. but have other FG members gives out minor tasks. Think the argonian DB assassin who wanted you to kill the argonian near leyawiin ie none essential and optional.