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I'm an assassin/stealth too. My setup is the Dark Brotherhood armor, (switch between the cowl and hood depending on the mission), dual wield Elvish Dagger and the Blade of Woe. I also switch that out for the bow called Finirel's(spelling?) End, which you can find on the ground in the top area...
@parker there shouldn't be an apostrophe between the n and s in dragons. Anyway, I chose the wood elf 'cause elves are awesome and I don't like the high elves or dark elves, and wood elves are good at archery and have natural resistance to poison and other stuff.
Probably the Kajiit. It has plus 10 sneak and plus 5 archery or something like that... sneaky guys :) I'm a wood elf and they work just fine, though they have a decrease with melee weapons.
Here's how I joined the Dark Brotherhood. I know there's other sources you can get this from but this is my take.
First you'll need to get the quest to talk to Aventus Arretino, a young boy in Winterhold. You'll find him performing the Black Sacrement. He'll tell you to go to Riften and kill...