This is my first exposure to Elder Scrolls. I really enjoy these story lines, and wonder what it would be like to run thru TES IV now. Just how far advanced is the gameplay in Skyrim over that in Oblivion? What would I most notice about the mechanics of the game? Do you think that Skyrim is so superior to Oblivion in content that I'd be really wasting my time? What would make me say, "This was a royal waste of time and money?"
I suggest you post this kind of thing in the Oblivion General Discussion forum, if you want the perspective of people who have played Oblivion a lot. Then you can combine it with the reactions of people who have done as much with Skyrim.
For myself, I wouldn't say that Skyrim advances gameplay over Oblivion, anymore than Oblivion does over Morrowind, etc. The changes to each title weren't based on advancements, but on perceptions of increasing market size and contouring features already present to match player profiles. There's no "superiority" to argue, just different experiences. I will say that, given the sheer wealth of mods out for Oblivion (over 25000) by this time, it does offer the ability to tailor one's playing far more than Skyrim does. This will certainly change as time goes on and Skyrim becomes heavily modded, but for now, if you want, say, an additional 100+ hours of involved questing, or the most deeply realized companions around, Oblivion's got these.