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It's not so much the mechanics of the quests since they all involve fetching, killing, fixing, rescuing etc.
Rather, its the humorous aspects of the quests that makes Oblivion stand out. Skyrim's quests are dark and humorless, befitting a story in a time of war and division.
Oblivion can make you smile or just laugh. For instance, there's the Destruction Trainer who talks about her destruction spells and using them on Kynareth's litte woodland creatures.
Or the Countess of Leyawiin who, with a big smiile on her face, enourages you to 'kill, burn, loot' the County's enemies.
Lots of goofy stuff too. Like the time I was collecting sacred lotus in a pool in the Imperial City.
There had been a Red Dawn event. All of a sudden, a head pops out of the water and says, "Hello". I nearly wet myself and almost jumped out of the chair
I thought it was some sort of developer Easter egg or something like M'aik. Turns out it was just an NPC who got knocked into the water.
You can't fight underwater in Skyrim so that limits your exploring. To catch slaughterfish, I have to use myself as bait and let my flame atronach kill it.
And Skyrim somehow feels smaller, but that's probably because a lot takes place underground.
Some of my favorite quests in Oblivion are from the Thieve's Guild and Dark Brotherhood questlines. Poisoned apples are really fun to play with.
I don't have any favorite quests in Skyrim.
It also has the best world I think. Walking around the roads/cities in Oblivion is so soothing. It feels like the calm, chilled out feeling you get when you're nice and relaxed at home.
And the Oblivion plane itself is awesome. It's like hell. You can go in there, smash up some demons and close that shi* down and get a great enchantment reward at the end!
Like 99.99% of people who have been Elder Scrolls fans for that long still claim it is their favourite. Including me. I would kill for a remaster--- but it would require basically remaking the whole thing like a new game with a new engine and all. But I would absolutely pay money for that.
There's already been a remaster for a while now. It's called Morroblivion. It's fully completed, stable and everything. It's Morrowind in Oblivion's engine. Not perfect but it's a massive improvement on Morrowind's engine.
I mostly like killing quests, because I like to smack everyone with the fists. Why Skyrim doesn't have that? What would be 10/10 for that.
But back to the point. I am not a fan of getting many single side quests. I usually try to get guild quest. Why? Well, since this game doesn't have acheevos, it's just a playthrough then. All guild from Mages to Arena, thenain quest. Dlc usually stands between them. It was since my first non-Steam playthroughs from 2010.
The only advantage Morrowind's quests had came from the diversity of factions. You could go on noble quests for the Imperial cult or rise through the ranks of the imperial legion.
The Expansion quests were also quite good, but that's to be expected with a much tighter project than the base game.