Ok, so I've replayed a fair bit of Oblivion and I haven't really wrapped up any guild questlines or the main quest nor Shivering Isles but so far I don't think that the game is necessarily badly written. There are an absolute avalanche of problems I have with the game but the writing isn't necessarily the problem because the game is so simplistic in its setting and design that it is hard to hold it accountable really. It's not like Megaton being created by dragging massive hunks of metal pieces from planes from an airfield miles away and then living with cultists around a nuclear bomb in the town square. Nah it's like, here's a town, it's been here a while, it does its thing as medieval fantasy towns do. Like, I can't really criticize that too much.
But the problem instead is in its design. Every location feels like a bubble, where things are so selfcontained that the outside world might as well not even be considered. I'm thinking of the major towns and the counts that exist. Who elected them? Why do they hold power? Who are their vassals? Are there any political intrigue behind the scenes? Some Game Of Thrones esque stuff. The vast majority of the time the nice cozy Oblivion music plays and everyone just walks around like
There's no teeth to it. No grit. The towns start to feel disengenuine the more you explore them. They mention that the towns of Anvil is full of drunks but I never saw any drunk sailors puke on the streets or sing shanties or try to grab a fistful of titty from a barmaid. I never see any real class disparity. In Skingrad there are two competing wine orchards and neither of them really have a bad word to say about the other.
Oblivion's problem isn't in that the writing is bad, it's that the world design and setting is bad which in turn makes the writing feel boring and hollow. Each town is designed to basically fit the same mold of what a town should be and then anything unique or interesting is tacked on as an afterthought without the town being designed for it and it shows when you play through it.
It's hard to describe a "feel" but the "feel" of Oblivion is cozy to a fault.