I would love to see this return in some form or another, but I'm not getting my hopes up. It worked in Daggerfall because the world was so enormous that you could be sent to a practically infinite number of locations. In a gameworld the size of Oblivion, you would end up going to the same locations over and over again. However, Oblivion showed that Bethesda was making at least some effort at having guild activities once you'd completed all the major guild quests, so let's hope they go much further in that direction for Skyrim. If infinite repeating quests don't make it in, it would at least be great to see some minor guild quests that don't tie into the overarching guild story. I do enjoy the guild stories, but I have to believe that some members of the Fighter's Guild just sign up to fight monsters in dungeons.
As much as I would love to see a randomised quest system in place in Skyrim the lack of locations would be a huge problem. In Daggerfall depending on your region there could be hundreds of dungeons (Wrothgarian Moutains had over 500 or something alone!), most of which took over 2-3 hours to finish searching depending on whether you got bored and cheated or not. I don't think it would be possible to generate such a large amount of dungeons with the detail which Skyrim will have. Plus even if such as large amount of dungeons were possible to be generated many people complained about most of Oblivion's caves/ruins having no story or real purpose in the game; these complaints would only get louder as the majority of those generated dungeons would be completely generic as they would likely be untouched by most players who hadn't recieved a quest to go there.
I hope they figure out a way of doing it as gives more purpose to joining a guild other than wanting 100% completion (maybe when joining the guild a set number of contracts must be completed each week or you are warned/kicked out of the guild, until you are a high enough rank to decide yourself when to the jobs for "lesser ranks"), but the only way I could think of doing it and making it remain fun for the whole game would be some sort of dungeon which is randomly generated each time you step in and obviously that would make no sense from a role playing aspect. Maybe there should be much more tasks which would be taken care of outside of dungeons (fighter's guild example to hunt down a nearby highway man or monster terrorising a nearby road).