I have several NPC's who I want to tell stories in taverns. I will start with getting one of them working then adapt the others. So my problem is how to kick this off to start with. How do I get an NPC to go and sit in a chair in a tavern every night at 2200 and start to tell his stories. It would be more helpful if I could have a random story so that the NPC will pick a random story of let's say five or six. I can do the dialogue etc, but setting the scripts and so on is proving puzzling.

You may check ArmandChristopheScript for ideas.

The script uses http://cs.elderscrolls.com/index.php/Say-http://cs.elderscrolls.com/index.php/SayTo-http://cs.elderscrolls.com/index.php/Lookto make Armand say a series of lines, one after another, to the Thieves Guild candidates.

TGArmandMidnight is the AI package that takes him to the spot every night at 11PM

And there are a few of Martin's speeches too. When he first addresses the Blades at Cloud Ruler, the battle prep at Bruma.

We've got a long cutscene in Dark Brotherhood Chronicles too, but ours has several NPC's participating, which I don't think you need.