My first RP project for Skyrim was Rowley Eardwulf, the Vile Lair DLC merchant from Oblivion... Just after the death of the Cyrodiil champion, Earwulf reclaimed the lair for him and Sithis offered him a deal: eternal life for a quest to destroy the Dark Brotherhood and bring honor to the Crimson Scars once more. So he has accepted, and tracked down every remaining member of the "family"... for 200 years infiltrated on every city, farm and hold to seek DB traces... and even though with a thirsty of hundred years, avoiding identification. At last he heard of a strange man had left Bravil packed with a huge sarcophagus heading Skyrim. So he decided to follow him and give the final blow against the Night Mother by kidnapping and desecrating her body. Everything went according to plan, he even succeeded infiltrating on a local anarchic group traveling behind the keepers carriage, his guise just to avoid suspicions. But then an awful coincidence took place...
It was an extremely difficult role since I love the Dark Brotherhood and want to finish the questline with every character, funny experience tho...
Its very easy to RP a nord, once Ive RP'd another Uriel Septim's bastard son, vampire, that ended up visiting Skyrim to meet his ancestrals home province. Very disgusted about how Martin Septim was the only recognized bastard son (and all the "sacrifice" talking) he lived in reclusion, contracted the porphyric hemophilia at some point of his journeys and lost a lot of his memories along the centuries. But kept his pride and as soon as he knew about the Stormcloak fight, started to camp with them, what eventually got him in trouble with the Empire.
Addicted khajiit skooma dealer/trader is very funny

my favourite so far.