I currently have 29 hours in my Red Guard Warrior/Archer and he is lvl 30. Whenever I need to train some skill up i tend to go to Markarth and tick off all the guards there and bring them outside the city to fight.
Now I honestly think there are more than 20 guards when I do this and I would stand no chance if it wasn't for my horse ShadowMere (Dark Brotherhood Horse). That horse seems invincible!
I've done this a couple times and i just recently looked at the bounty on my head and it has come to 48,080 gold. So what is your largest bounty you have had on your head?