First off, you wil notice that Talmberg is highly supervising you and your actions, they wont let you out what so ever, so there is basically no good income from trying to talk through that, cuz none of your speech and charisma efforts will do anything, Sir Robard is too much of a warden to let you out.

Second off, DO NOT, and I repeat, DONT take or try to complete any quests besides talking to Sir Robard once you reach him in near the arena. Then, the secret magic happens! See that drawbridge that connects between the 2 castles in Talmberg? (one is more fortified and the other is for residents), well then as you can see you can jump off the low parts, but you can crouch through the higher parts(where the chain is in a higher position), just do this stealthily and carefully because once you are seen, you will be sent back to prison called Talmberg. Once you are out and unseen, you may sneak all the way out until you are at least 100 meters away from the fort.

Now, IF you get caught, THAT is what you ought to do:
1) Pay him if you got enough $$$.
2) Fight him with your damn fists(a very bad idea).
3) This only works once, but you can convince a guard to let you off with your speech powers(if you have any).

This quest in general, is very cheesy and glitchy and very easy to mess up, that is once of the quests I hate the most, and I'm glad I am through it and I can share my knowledge to you.

Thank you for reading my guide, I really appreciate it. Now one of the people I want to thank is JonathanWhiting13 who helped me with huge parts of what I have done to gain the knowledge I am sharing to you right now.
Enjoy your lives nad have a good day/night!