Ebony dagger (use if you must)
Fist (throw in some quick jabs and run away)
Blackguard hood you need sell those obtained goods
Blackguard armor you actually need to carry those goods
Blackguard gloves how do you expect to get your goods buying them
Blackguard boots just take it so you don’t need to pillage their corpse
How to play
You steal of everything of value Septims, gold, jewels, amulets, rings, necklaces. You store your Septims in a safe in your house. If you get caught robbing a house and the owner is attacking you throw a quick punch or two and run for your dilly dilly life. If you get caught by the guards take some time in jail then escape. If it’s worth some value take it don’t matter if the the goddamn high Kings widow wedding ring take it unless it’s worth less then 100 Septims then don’t take it just thief logic.
Nearly everyone in your family was a thief except your mother who supported the family with other means. When you were a young lad your father taught you how to beg for gold wasn’t a lot but enough to survive. Later on you were taught how to cut purses now that was a way to make a fortune. While growing up your father didn’t think it was necessary to get a education as he always said “if you can cut purses and rob people you don’t need one, unless you want to become some milk drinker merchant. You and your family wanted nothing with the fighters guild because why protect some snot nosed merchant when you could rob him for so much more. By the time when you were bout 14 you started breaking in entering which gave you some time to escape from the jail cell you were placed in. So many years you spent robbing and pickpocketing you loss count of how many punches you had thrown while the owners had catch you. One of the owners was a strong looking man you quickly kicked him in the genitalia and socked him in the jaw and ran for your dear life. Your father was a stubborn man never taking handouts and never backed down from a fight had few bruises on his face. He had always despised the fighters guild and the mage guild always thought they would be our downfall of thieves.
By the time you were 21 your mother died of rockjoint. Before the age of 14 your partners in crime were your family after you and a childhood friend starting doing crimes together mostly breaking and entering the nobles house. Later that year your father was killed by the guards after punching one in a drinking rage after drinking away his sorrows you left cyrodiil and headed to Skyrim at the age of 22 but not before taking the head of the guard that killed your father then you got caught in a imperial ambush