See, this is what I thought also, they don't explain the quest too well, or allow you to select too many of the line of quests from him at once. The trainer is him, why he says "your trainer, or "trainer" i have no idea.
What is supposed to happen is, you get the tutorial quest, then you select the other information quest, apparently the information quest (get 2 Hearsay for Blackmail) IS the first step in the tutorial quest and you have to complete that one to get to the second part of the tutorial. However, the next step requires too much noble (or another presence, can't remember) presence that I don't have and i can't even do it.
And it seems being at skin level 53 i'm starting to get ones that require skill level 60 or higher, i know that's not too hard for me probably (still a beginner myself really, lots of stuff to learn) but i'd rather not be kill on site by my own city anytime soon, it's hard enough as is.