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Marry a nord woman then murder her on your doorstep, get away with it. Disappear for a long time before resurfacing at the Bard's College with a song about your pet Sabercat. Drink lots of skooma then rob the general goods store in Solitude.
Might want to do the quest for Eola in Markarth to get the ring of Namira. If you join in with the random encounter just make sure you het the ears. Gather up Falmer Ears to make potions in alchemy. Resist Foison and Fortify Lock picking. I know they can be used in poisons as well but Mike would probably think they taste too good to use in poison.