For whatever reason, there have been a few posts lately about Oblivion's levelling, game mechanics, etc. I just wanted to show an alternative approach to starting a new character. Okay, bear with me here.

See, when I started playing Oblivion I always used to choose or create a class based on the type of playstyle that character would use. Assassin? Choose stealth skills (sneak, marksman etc). Mage? Choose magic skills. You get the point.

These days I tend to pick a class that has more to do with their character, regardless of the impact that will have on gameplay. This was most vividly brought home when I made my most recent character:

There was a young Nordish goatherd who lived simply and tended his flocks in Skyrim. One day a starving bandit approached the goatherd with weapon drawn, his intentions clear. The goatherd instinctively reached out his hand and shouted "Stop!" The bandit stopped in his tracks, sheathed his weapon and looked around bewildered. Eventually the bandit wandered off. The village healer observed all this. Realizing the boy's potential, he brought the boy to his humble house. The boy quickly learned all the healer could teach him: an assortment of simple healing spells and how to light a path in the dark. The healer admonished the boy to travel to the heart of Cyrodiil, where he could truly learn to be a great mage. He gave the boy a new name: Farbrecht. Farbrecht sold his herds and travelled to Falkreath where he met a travelling merchant carrying pelts and cloths and assorted alchemical ingredients both common and rare. The merchant allowed the boy to accompany him over the treacherous pass to Bruma, where he introduced him to an innkeeper named Olav. Having arranged a room for the night, he was just settling down when commotion erupted all over the city. Word had arrived, "The Emperor is dead! We have no Emperor..."

So begins the story of a young Nord who improbably ascended to become Archmage of Cyrodiil and one of the most powerful conjurers Tamriel had ever seen. With the story arc set, I made a false start by creating a character with the default mage class because those are the skills he would play with. Then I realized starting this character as an apprentice in all the magic skills was skipping over a big part of his story that I wanted to experience. I went back and made a character with a custom class called "Goatherd", based on the backstory:

Athletics

Acrobatics

Blunt

Hand to Hand

Block

Restoration

Illusion

I have no idea how that will effect levelling and I don't care. I just wanted to choose skills that would be at the appropriate level for this character starting out. I did choose the apprentice birthsign to reflect his natural talent for magic, but I wanted him to enter more or less as a novice in the magic arts.

So I wondered: Do you choose your starting skills etc based on how the character will play? Based on the game mechanics (levelling etc)? Based on who the character is or will become? Do you craft a character to fit the skills you've already picked?

(Note that none of these things are mutually exclusive; my long-running spellsword has a quite a developed story and the vanilla class fit both his backstory and his playstyle perfectly.)

I choose Alchemy, Conjuration and Illusion, because these are very strong skills and then four others depending on whether I want a warrior, a mage or a stealth character.

I like playing charecters with mental flaws.

Like, my mage character is afraid of the dark, freezes up when trapped in the dark.

Or my Ranger character hates large towns. Makes the game a bit more exciting that way.

If I'm reading your post right, this is basically what I do too. Or, to put it another way: I play characters, not classes.

More and more, when I start a new game I think of it as writing a story using the tools the game gives me. I create a protagonist, and create conflict for that protagonist to overcome. This conflict can be in the form of an external obstacle (such as finishing a uqest, clearing a set of dungeons, ect) or internal (overcoming prejudices, fears, learning to accept oneself, ect).

And more and more I find I am not only interested in characters that are flawed or ambiguous, I am also more and more interested in characters who change in response to the events they experience. A breton character might renounce her magical heritage to become a warrior...but during her adventures finds that her ability to manipulate magic has benefits she never considered before. These types of ambiguous, changeable characters are what fascinate me most these days when I play an Elder Scrolls game.

To borrow my friend Shelly Mars' terms, I take a roleplaying approach to chargen creation rather than a gameplay approach to character creation. In her schema, the roleplaying approach to character creation is to pick skills and birthsigns that the character will use, that reflect that character's personality. The gameplay approach is one in which we pick skills in order to achieve a desired gameplay effect, such as slowing down our character's leveling speed.

So when I create a character nowadays I select chargen options that best reflect that character. I attempt to use the chargen tools the game offers me to try to reflect my character's starting personality traits. I give no thought to whether this will make the game harder or easier, slower or faster, ect.

That's a fascinating background. It reminded me of the story of King David. I think your choice of skills is appropriate to the character you've created and with a start like that it should be an interesting experience. I would suggest you take your time and develop him in a way that is consistent with the background story. The skill set he has now may not be the ones he carries forward as he progresses but that's fairly common IRL. His pastoral past may be nothing more than a rite of passage before arriving at his true destiny.

Another idea is to go here:

http://www.uesp.net/wiki/Oblivion:NPC_Classes

For some ideas on making classes.