After hours of nail-biting deliberation, beer-drinking, about seventeen bags of double-stuffed Oreos, beating up a few old people at Wal-Mart, and a few really nasty bodily functions, here's my take on the whole damn situation.
How to address the http://www.uesp.net/wiki/Oblivion:Efficient_Leveling? (the theory that your character will become less powerful compared to high-leveled monsters if you don't get those +5 attribute bonuses from training the right skills).
Ultimately, I decided that it's not worth the extra time to worry about it. Why?
1) Elder Scrolls games are only fun if they're a challenge, especially Oblivion. You don't really need to level efficiently. Unless you have this crazy craving for that perfect character, it's just not practical. In my opinion, the game's way too easy out of the box, and the "difficulty slider" is anti-effective. So I'm using http://www.oscurogamedesign.com/oscurosoblivionoverhaul-high.html and loving the realism. You gotta be careful and pay attention, to win with this difficulty. No more "awww, it's just a wolf on the road, how cute..." instead... "he's gnawing my reproducer!"
2) An ?ber character's not challenging, other than the time spent clicking a button to train a skill. No one character should have the ability to handle every situation. Hell, if an ogre runs up to my Endurance-low mage and shows me his armpits, I'm running my bare-ass out of there, because it makes more sense that way. I guess I enjoy that bit of roleplaying.
3) I'll spend more time worrying about Efficient Leveling than I will enjoying the game. I found myself sitting in a room clicking "cast" for hours, thinking oh man that +5 is gonna be sweet, while not taking that call from my boss who probably wonders where I am.
So if that's not enough self-justification for ya, let me go further into detail for anybody who's not in a coma by now.