Well, like I said in your Restarters Anonymous thread I don't think there's anything wrong with restarting. I think restarting new characters is fun, I enjoy it. And I tend to bristle at the assumption that there's something inherently wrong with restarting. I've had people tell me "If you restart too often, you're doing it wrong." Nonsense. If you're not having fun you're doing it wrong.
As for what character you ought to play now, I think that ought to be up to you. Play whatever seems the most fun to you. If this one catches your fancy and you end up playing it for 300 hours, that's great. If you drop it to start a more interesting character after 10 hours, that's great too.
You're not alone about Shivering Isles. I haven't played Shivering Isles either (and I've owned it since the day it came out). I haven't done the Dark Brotherhood, the Mages Guild, the Thieves Guild or finished the Arena (I have never seen the Adoring Fan). I haven't finished Knights of the Nine or done the other DLC quests. I don't think of this as something to be embarrassed about. On the contrary, I actually feel kind of sorry for gamers who impatiently whiz through a game's contents in a matter of days or weeks or even months and then feel that there's nothing left to hold their interest anymore. I like to take my time with games, to savor them - especially ones as rich and diverse as Elder Scrolls games. I have a lot of Oblivion left ahead of me still, and that's exciting to me. I'll still be discovering new things when Skyrim is released.
Anyway, good luck with your next character. I hope you have half as much fun starting a new one as I do.
That bolded part resonated with me so much, I just had to respond to it. Thanks for posting guys.
I know both of you probably have played Oblivion a lot more than me, but with something between 600 and 700 hours of play, I have to admit that, sharing these same 'deficiencies' in 'achievements' in the game world sometimes seems a bit worrisome to me subconsciously.
Then I get excited to go back and redo a new character

Had my most recent character get killed last night *sigh* Seith Ethyniriel, brother to my last character, who also died. Seith got killed by the Vilverin thug leader. Damn that guy is tough with OOO.
Torn now about restarting with a new one. The Good Samaritan did not save me in this case, so it will be a breach of my dead-is-dead resolution to keep playing him. Still, the idea of redoing Level 1 through 3 with yet another character seems a bit off-putting too. I think that is the main problem with restarting, but the more I think about it, you don't necessarily have to do it that way. With the console you can basically 'skip over' any of the early game quests that you want and have them be 'finished again' without doing them again.