Update: level 10 barbarian / level 2 mageblade (I remade him and took suggestions from a strategy guide I found, and took their name!)
10 hours so far on the level 10, and like, 40 minutes on the level 2.
The level 10 is grand champion of the arena, is a silencer on the Dark Brotherhood, a journeyman on the fighter's guild, and starting ranks for the Blades/Mage Guild.
Someone wanna point me to the Thieves Guild? I'm gonna complete that after I complete the Dark Brotherhood quests.