Alright. So I have this nasty habit of planning EVERYTHING out, and I need help with my character. I have made one for each race, and I can't decide which to pick.

Argonian Scout (1h, light armor, sneak, lock-picking)
Breton Conjurer (1h, Heavy armor, enchanting, conjuration)
Bosmer Archer (Bow, light armor, sneak, alchemy)
Dunmer Spellsword (Heavy armor, 1h, enchanting, destruction)
Altmer Mage (robes, most schools of magic)
Khajiit Brawler (Heavy armor, enchanting, unarmed)
Redguard Knight (Heavy armor, 1h, shield)
Nord Warchief (Light armor, 2h, smithing)
Orc Berserker (Heavy armor, dual wield)
Imperial Looter (Light armor, dual wield daggers, pickpocket, lock-picking)

First one to reply I will pick.

Go with the Argonian. Argonians are win!

All of the races work pretty much equally well with only occasional slight benefits for one or another in various scenarios (Orcs can enter Orc strongholds without proving themselves, and Altmer can disguise themselves as Thalmor at the embassy, for example) but, in Skyrim, Nords feel the most natural for me. You're wielding a power that is virtually only ever attributed to Nords, you're optionally participating in a Nordic civil war, you're going to be surrounded by Nordic this and Nordic that for the entirety of this game. It was the same for me with Dunmer in Morrowind.
Lots of people have other preferred races though, and they are perfectly happy playing them, so it's not the right way, but it's the one I'd recommend as the choice I found to feel most natural. Plus, the cold resistance and battle cry powers kick ass.