My adventurer went back to the goblin pits to rescue a lost companion only to discover that he had been killed just a few hours before. She kind of lost it and did the whole Anakin Skywalker thing. Since her goal is to bring peace to the world (not balance to the force!), she decided to become a travelling bard, give performances to Lords and Ladies and avoid conflict if possible.
I discovered a couple of things. First, I think that bragging about your violent deeds seems to be fixed. I bragged about a few things and was careful never to spread rumours about those things. I noticed my companions talking about them and fairly quickly my reputation preceded me. When I showed up to a town and asked about myself, many times they already knew about that act. This is great because it saves a lot of time scrolling through the rumour list.
I also noticed that when you notice a robbery, you can report it using the rumour list. I never realised that before. I'm going to keep a closer eye on it in the future.
As for performing, I've had terrible trouble increasing my speaking skill. Stories seems to improve it almost imperceptibly. After hundreds of stories, it had grown only about 10% the way through novice (starting at novice!). When I started to mix poetry into the mix, I got a lot more success.
In order to learn new stories, the way to do it is to ask people about the current, ruler, surrounding area and the structure that you are in. This seems to top you up with stories about the area. You can ask more than once and will often get different information. After that, you can tell stories about anything that you've asked about.
I discovered that people have preferences for types of poems. Possibly it's related to the "Likes to hear the sound of the Pregnant Willows" that you see in fortress mode. The interesting thing is that if a poetic form has riddles and the listener likes riddles, they will say so. If they like sombre poems, then they will hate light hearted poems and will also say so.
I started trying to select poems, songs, dances and stories that would appeal to the lord/lady I was performing for. I looked at their reaction and then tried to divine what they would like to hear/see next. Not only did this make performances a *lot* more fun, but it seems that my speaking skill improved *much* more quickly.
I don't have any real evidence yet, but I suspect that pleasing your audience is an important part of improving skill. Must experiment some more...