I don’t know if you guys have this planned, but you should introduce a reputation system: As you fulfill contracts, you reputation grows and you get to access to harder quests. Once you acquire a certain level, you should be able to target (or be targeted) a rival mercenary band (Boss Battle).
Once you defeat the rival band, your band levels up and get access to better quests.
The system you suggest reminds me if shadow of mordor, which would work really great with our simulated world and the rivalling factions in it.
We are discussing a two fold system wirh a ‘proffessional’ reputation and a ‘moral’reputation. Your deeds will then affect these values separately.