So I made this new character who I'm going to freelance with for a little while, he's a Nord Ranger and Bounty Hunter. I've been going to the Bannered Mare, asking for work, getting bounties, clearing out the bandit hideouts, and finally getting the payment from Proventus.

My question is, can these contracts run out? What happens after I've cleared every bandit hideout in Whiterun? They start over? Or they're always empty from then on?

Also while I'm here, what level do you think I should start questing on? I'm talking about good leveled loot, strong build, decent perks, etc.

Good question. I am also interested in the answer to this.