So are we doing this just in Skyrim, or all of Tamriel? Lore isn't a problem, I'm Elder Scrolls educated (I speak fluent Dovahzul). It's just whether we want to do something that big.
Well, maybe not every province. But the ones surrounding Skyrim, which are High Rock, Hammerfell, Cyrodiil, and Morrowind. I mainly mean Cyrodiil and Morrowind, but High Rock and Hammerfell could as provide good hiding places or searching places.
*Sighs* I should probably change my sight to 'Elder Scrolls Geek: Services Available, FREE!'
Haha no worries. I may not be as knowledgeable as you are about the universe but don't let it hold you back from doing anything you feel like writing about. Google is my friend.
In your character's bio it says he's heading to Winterhold so on the way, or there, both of our character's could get caught up in something? I can't think of any sort of specific conflict off the top of my head yet, besides random dragon encounter.