I have never had my OCD spike up this severely in years. For some reason in Oblivion, I was able to create a character, and not scrutinize it too much.
Skyrim, however: Character creation really has me hung up.
I have probably created a dozen or more characters since launch, and have never been satisfied with a single one.
I am to the point of having a piece of paper and pen, writing out how many slider counts should be notched in which direction.
I have rerolled many times just because my character's nose was one slider too high or low, hair styles, etc.

As for gameplay, I couldn't be more satisfied with the immersion. I have been content with just trying to find/collect all the clothing sets/shoes/boots, let alone quests.

For build, I prefer an all purpose, balanced build. I have never believed in specializing in one direction.

The first character I create in any RPG is always the same: an aging ex-soldier who uses a sword and shield who always goes by the same name if the game allows. I consider him my alter ego

After that I either I look to movies/comics for inspiration and try to recreate the certain characters while adding my own twists, or I will try to create certain archetypes such as the wise wizard, the evil assassin, or the common thug, etc. and then decide which race, weapons, skills would best suit that character.

I haven't run out of ideas yet

I have a basic foundation of what I want to play in RPG's (typically a Necromancer of some sort), and then I determine from there what else I'm interested in playing as well as what game mechanics appeal to me. In Morrowind, I played a stealthy Bosmer necro-assassin that eventually just morphed into a standard thief / assassin. Marksman, Light Armor, and Short Blades were the focus of my combat, with Conjuration and Illusion as magical support. He was an anti-hero based heavily on characters like Gambit (from X-Men) who did bad deeds, but ultimately had a good heart. He didn't believe, nor care about the Nerevarine prophecies, but after doing work for The Blades and becoming more engulfed, he finally decided to seek out Dagoth Ur for revenge from the Sixth House coming after him trying to eliminate him. His quest for Dagoth Ur became one of personal retribution. In Oblivion, I tried a lot of different types of builds before I figured out what I wanted to play in that game, which ended up being a Redguard tank necromancer, or shadow knight. A warrior with two handed swords, heavy armor, and lots of magic in Conjuration (obviously the necromancy aspect of summoning undead spirits), Alteration (Shield spells), Destruction and Mysticism (manipulation of souls; soul trapping, "sensing" souls [Detect Life]). The roleplay was essentially a shadow knight that summoned evil spirits to aid him in combat, as well as steal the souls of his victims to harvest their energies to boost his power. He became corrupted by those powers, and went down a path of darkness. Skyrim was basically a mirror image of my Oblivion character; a Breton shadow knight with ultimately the same build - One Handed (Dual Wield), Heavy Armor, Conjuration, and Enchanting were the focus skills, with support from Alteration (shield spells), Restoration, Smithing, and Illusion. Illusion wasn't part of the original build (which unfortunately was lost during an accidental X-Box 360 hard drive wipe), but was something that I wanted to include, so it's been in later versions of the build. Unlike my Oblivion character, where the roleplay was a man who succumbed to temptation and darkness, my roleplay in Skyrim is of one who resists all that, harnesses these great powers that are considered "evil" but he uses them for good. The powers (Conjuration, Illusion) represent his command over souls and mental domination, even Alteration a bit (with Detect Life spells), and Restoration is representative of his "good" side (as opposed to Destruction for my Oblivion character), as well as further domination over undead. I just like the idea of Shield spells to add to my already beefy armor rating (even though I don't think by end game that Shield spells will give me too much more armor than my heavy armor). So it's really just figuring out what type of Necromancer I want to make. When I played Morrowind originally, I was real into stealthy, assassin type characters, so I combined that with my necromancy, to build a necro-assassin. More lately, I've been more into tanks and heavy armored brutes that can get up into the thick of things, so that has led to my shadow knight builds. My racial choices are a mix of roleplaying and best fit, and the "detail" skills are based on a mix between what I want to accomplish in game as well as what game mechanics I want to take advantage of.

I have major restartitis. Like, it's a problem. I don't know why, but for some reason my restartitis is only active when I play Skyrim. When I play Oblivion, I'm usually able to make a character and stick with it. I just gave Skyrim a break for the past month or so and have been playing Morrowind during that time. WIth the same character. He made it to level 32 or so, owns the Thieves' Guild, and just beat (I think) the MQ. I'm not even sure I'm done with him yet. But in Skyrim, it sometimes takes me 3 or 4 characters before I stick with one for more than the first 5 levels. I haven't made it out of the low 20s in level yet, with any character in Skyrim. Again, I don't know why this is. Maybe it has something to do with the lack of character classes. It's so easy to just play whatever you want to do that there's no 'need' to plan out a character build. But I try anyway. I have a notebook with about 20 pages full of character ideas, most of which I haven't tried yet. I get a lot of character ideas from other rpgs. I'll take a character class from Pathfinder or D&D like the Arcane Archer, or Shadowdancer, or Paladin, and see if I can replicate it in Skyrim. Or I'll look through the uesp's list of premade character classes for Oblivion and Morrowind - like the Crusader or Nightblade or Witchhunter - and try to do that in Skyrim. Or I'll come up with something that just seems fun, like archer tank, or travelling researcher. Once I have a basic class concept down I jot down the 'build' - the race, name if I can come up with one, and a few keywords that indicate the type of character. Then I list main skills, along with any notes about how they should be used. Then I list minor skills, if any. Finally, I'll write down a rough idea of any RP ideas or restrictions I have - like no magic & scrolls, or no sneak archery, or kill stuff with staves. And I'll note which guilds/quests I should do with the character. It's something to do when I have some free time, anyway!

I have half a dozen different characters that I am actively playing in Skyrim right now. I typically get an idea for how to perk a particular character in advance, choosing about 50 perks that I think will get good synergy together. Then I decide a race and just a little backstory. I build the story along the way as I play, depending on the random events that I encounter during the the game. For example, my latest character is an Altmer robed mage, forcusing primarily on Destruction, Restoration and Enchant. He wears robes out of choice, since he likes to move quickly and doesn't really believe a mage should be wieghted down with a suit of armor. At first, the only weapon he carried was a dragon priest dagger, and the only time he used it was when he ran out of magicka, which was rare. Well, when he was about level 20, he encountered his first (and so far only) draugr deathlord. It was an epic battle, and the draugr was wielding an ebony greatsword (thank goodness it was not an ebony bow). Such a find at relatively low level was a unique and interesting event. My mage ditched the dragon priest dagger in favor of the ebony greatsword. There was a story behind that sword and how my character got it, so it had sentimental value. I'm level 40 now and I still have that same ebony greatsword. Since I am a mage, I am not that good with 2H weapons, and I don't put any perks in that tree, and I rarely use the 2H sword (although I did pay for some training and I smithed the sword, unperked, but boosted by enchant). But I always carry that sword, even though it is heavy. When fighting other mages who eventually draw daggers on me, I always pull out the 2H sword and show them what's what. The ebony greatsword has become a thing with that character, and it helps define who he is.

Mostly, yes. I will create some secondary characters that I toy around with a little bit, but I'm pretty much a "one character" kind of person. I just build a character that is both the type of character I want to play (I.E.: necromancer), as well as would cover the content in game that I want to experience (I.E.: Mage's Guild...)

Yeah that's pretty good. I do like the theory of hunter/warrior/bounty hunter type but I can't break the fact that I need to heal myself. It's like a bad ex-gf I can't get rid of.

I tend to start with finding a good sounding TES name, I look though mythology and history to find an appropriate name and personality. for example if I wanted to play an Imperial assassin, I would find a Roman character and name them after him/her Marcus Brutus is my assassin/speech character and he stabs emperors in the back. If I want to play a breton I look though french/frankish history. the other races I am not sure where their names come from?

I started using tabletop RPG books in Oblivion to get a handle on the background of my character. I use dice to pick race and providence, then again to pick a day job, and another to pick my "class", and then pick my gender and move on. Since the ride to Helgan takes a long time, I use that time to go through my RP options. Current char is a Khajiit Spellsword from Cyrodiil, with a day job of Smith.

meh i get an idea of a character i like, ex breton enchanter. Then i start the game up, realize that what i really wanted was a breton conjurer who uses bound blade cause the bound blade is teh pimpest thing evur, thus changing my initial designs slightly. After a while i think that a sword fighter uses some kind of armor and slap on light armor, then i realize light armor after leather/scaled looks like sissy elven crap so i use robes and alteration. Thus i end up changing my character 90 degrees.

So usually i just sort of go with a vauge idea like assassin and play whatever i happen to think is fun, or get inspired by the char gen at the start and go from there.

I also like the idea of contridtions, so i go with imperial mages, orcish rouges, high elven barbarians.

And my first character is always a warrior nord who dabbles in magic, i find its the best way to explore the game the first time through.

with enchanting you can make your toon use no mana at all making that need to heal yourself FREE

I like your idea a lot. Thankfully, Skyrim made necromancy 10x more fun compared to Oblivion. It's a shame you can't use 2h swords AND cast spells like you could in Oblivion though.

Oh by the way if you want I can give you my findings on making one character that is DECENT in Magic, Stealth, and Combat. I don't mind giving you those skill trees if you're interested.