Alright so

"Gossip" can be attained at different locations around the town. At each location a diplomacy check can be rolled to see if you are able to get that location [person] to "pour the tea". You get one chance a day to roll for gossip at each location. Others may assist with diplomacy to give better chances.

As you can gather from your interactions from Brucian, a non-human aiding or being the main diplomacy, will have a higher DC to gain the "gossip" but its not cumulative, while aid another with diplomacy is cumulative, if you have a 1 main roller and the other 5 attempt to aid, you can provide up to an additional +10 to the main roller.

For how this will play out, you as a group tell me where on the map you'd like to go, and roll diplomacy. I'll post results, any "gossip" gained, and you can respond with any follow up questions, and any other things you might like to do at the location before heading to the next.

Your current location is marked by the small red circle on the map.