I just started doing the Dead is Dead.
My first one was a Nord farmer who just signed up with the stormcloaks and promptly got captured with Ralof and Ulfric. I figured I'd give it a try on mastery because him being an untrained farmer wouldn't have any proficiency with weapons. Also just picked from the presents and only changed the hair to the balding look. Things started out great while Ralof was helping us out, kind of like a big brother

...but then Ralof decided to stay in Riverwood and the farmer decided to make his way to Whiterun. After beating some wolves and a close call with a mudcrab he found a cave. (can't remember the name, but has that blind guy Ulf in the first room). slowly made his way thru the place and with his confidence at an all time high took on the bandit chief (who had a 2 handed sword). and two hits later the poor farmer's Stormcloak career came to an abrupt end. (level 4 or 5 i think it was)
The other was an old Orc warrior who was just looking for a good death

(no magic, potions or enchanted weapons. only steel for him, played on expert) . 3 Hired Thugs gave him that good death. After clearing out Halted Stream Camp, he just didn't have it in him (or the food for health) to make it thru another battle. Had fun with that character while it lasted though. (level 10)