I think I might make levels of certain types, like Militia, Watchmen and so on. Like hirelings, with 6, 12, 18, 24, 30, 36 advances etc.
For my current situation, I think I'll drop a few hints that being polite could have earned him a lot more reward, and possibly a patron. One of the other players has already been suggesting to him to keep quiet, and stop digging himself into more trouble. I might drop a few more clues, that the particular patron could have had more tasks and rewards that they've now missed out on for offending her