Im all in for randomly regenerated landcape, ruins and cities. Thing is that it gets boring when starting a new character for the 8th time, and you already know where to find all the ayleid ruins, shrines and caves.
Everytime you start a new characters is basicly a rutine.
Go to Vilverin when exit sewers.
Go to Weynon and talk to Jaufree Southeast of Chrorrol to get free items and free horse.
Fast travel to all mages guild to get recommendation ASAP.
Get to lvl 5 and go to Azuras Shrine north of Cheydinhall to get Azuras Star.
It becomes boring because you already know where to go without any real exploring. It doesent help that all cities are shown on your map right from start.
That's just the way you play it...
Most of my characters haven't even started the Main Quest. My characters don't join all the guilds. If it bothers you that you do this every time, why do you do it?
Is it nececry to get Azuras star that soon?
Just make a different kind of character or something. You do the same thing every time you make a new character and then complains you do the same thing every time.
I agree that Oblivion gets old quite quick, but that has nothing to do with random generation of stuff.
I don't randomized terrain at start up. Replayability is created with many intresting guilds, quests that have different endings and those endings all have impact. Not just the main quest and some other big quests, but many quests. Off course not all the quest should be epic and world changing, but the impact could be subtle and many quests could have multiple endings without it having impact at all (except rewards maybe) and quests that don't have multiple endings (but are well written and are fun to do.)
Oblivions terrain was quite boring for the most part, as if it was generated and they only checked if it was working and then some handcrafted places were added to it.
I don't mind having the terrain generated at he time of developing, but they should make sure it's interesting, and add unique places to it.
Randomizing it every start up so it remains 'fun to play' and add replay value is a bad idea, because a game that needs a new randomized world every new start to make you want to play it is a bad game anyway. The next TES should so good it doesn't NEED randomization. Though, to make it that good it probably needs generation at the development.