In this breakdown, I briefly go over Oblivion's often confusing leveling system and make it easier to understand the basics of it. There are still many more smaller confusing parts to the leveling system.
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How does Oblivion's leveling system work? Let’s break it down.

During the tutorial, you make your class and select 7 major skills, the rest become minor skills. To level up, you must level up your major skills a total of 10 times. The next time you sleep, you will see this menu.
Here you can select three different attributes to increase. The amount you can increase your attributes is determined by how many times you leveled a skill governed by that attribute. It takes this many increases in the skills governed for an increase in each attribute.

What Does This Mean?

For a casual player playing at mid to lower difficulty, you should strive to get 2 or 3 points of increase in the three attributes you pick when you level. This should keep you around the same level as your opponents.
If you’re playing on higher difficulties, it may be better to strive for plus 5s in increase.

To help keep control of leveling, you should choose skills you have easy control of as major skills so you can stop leveling if you don’t have your bonuses yet. Easy choices for these are Security, Speechcraft, Armorer, Alchemy, and any magic or combat skill you are not using all the time.

And please, use the Skill Diary Mod so you know what your bonuses are before leveling.

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