Theres a place outside riften where you can go on a huge murder spree without worrying about guards. you'll still get the bounty if anyone sees it of course.
Playing your character the way your character should play is all that matters. Play as well as you can but never betray the character. Doing so would make playing an mmoRPG pointless.
I have had a character with over 2.8 million bounty exploiting the stolen item quality after the changes where higher legerdmeign improved stolen item quality. An basic cash cow where group members would loot the kills without them getting a bounty; just have the murderer kill all "witnesses" Quest NPC dont report, so... have fun in quest areas too.