April 17, 2015 11:09 AM EDT
Things that are better in Oblivion than Skyrim:
* The faction quests, especially the Dark Brotherhood and Thieves' Guild quest lines. For that reason I think a sneak thief / assassin build is a great way to introduce yourself to the game.
* Enchanting / magic. Once you get far enough in the Mage's Guild questline, you get the ability to craft custom spells. It doesn't take much fiddling to figure out how to break the game wide open in the best way possible. Also there's a full set of Bound armor spells (like the Bound weapon spells in Skyrim), which is fun. I rolled a mage build once with a custom spell that cast all the Bound spells (greaves, chest, gauntlets, helm, and sword as I recall) at once. It drained my entire mana bar, but it meant I could switch between a glass cannon caster and a tank at will. Also, Destruction damage actually scales so that it is useful throughout the game, instead of Skyrim's busted-ass system.
Things that are better in Skyrim than Oblivion:
* The setting. Oblivion's Cyrodiil is a little generic compared to Skyrim's Nordic flavor, with a few exceptions (the Blades faction is way cooler in Oblivion). Also a lot of the random dungeons in Obliv are procedurally generated and not quite as interesting as Skyrim's, which AFAIK are hand-crafted.
* The combat, especially the melee combat. Skyrim already feels a little like you're swinging a sword through thin air as opposed to plunging it into the flesh of undead horrors; Oblivion has that same problem, but more so.
* The leveling / enemy scaling system. Oblivion makes you futz around with character classes in a system that's not very intuitive. It's also a LOT more naked about scaling the enemies, which can be pretty immersion-breaking. Skyrim does it too, but it hides it better. There are mods that purport to fix this, but I haven't tried them.
* The main quest. If you start to get really, really bored closing Oblivion gates, don't worry, you're not alone. The good news is that unlike Skyrim, which gives you all kinds of fun toys for completing the main quest, all Oblivion gives you is a suit of armor you probably won't wind up using, so you're not missing out on much if you eschew it altogether. If you do decide to go through it, protip: you can make a mad dash through the Oblivion gates without stopping to fight enemies and get to the exit unscathed.
TL;DR, I think they both have strengths and weaknesses and I think they're both definitely worth playing. I understand the Oblivion mod scene is also very strong, so it shouldn't be much trouble on a modern system to beef it up with graphical mods to make it a little easier on the eyes.