A good idea for a not so nice quest for not so nice Avatars. However, the amount Umberjack has leant out to his custumers needs to be higher. Umberjack woulnd´t be long in business if he leant out 100 gold and gave someone e.g. the last time: 83 of them for collecting them and a Cutlass in addition. Umberjack needs more customers. One person can perfectly alone collect the payments of 3 cusotmers in Broochash when it´s only 1 / day. He could do that alone. Umberjack should start to offer his moneylending business to all craftsmen, merchants, innkeepers and farmers in Drachvald and perhaps even Grunvald so that the daily quest is no longer limited to within Broochash. Let him expand like the Mafia (or the Triads for the Shogunate flair)...
Interesting suggestions! I probably won't go back to expand on this quest, but from a fiction perspective we don't know the actual extent of his operations. We only know that he asks others (such as your avatar) to assist him. You're not high enough rank in his organization to know if he's shaking down others for more money, or even the same people multiple times a day. Or maybe he's considered that he needs to keep things small because if he asks for too much, he'll get too much attention and someone will come to shut down his operation.
