Helgen, visiting it after picking someplace else, following the original route, the tower isn't broken (where the dragon broke through to roast a guy), the underground area, walking to go through a hallway causes the dragon to crash the ceiling to the floor so you can't go through.
The bed segment of your quest never finishes (may want to, as it looks incomplete, plus it's still targetable later). I was wondering where that quest pointer was aiming at.
For the outlaw in the wild, perhaps place another NPC that is non-combat (a bandit), that offers buying and selling of things? Since when you're out in the wild, its hard to find people to sell to that will when you've got bounties (and can't get into a town without guards after guards chasing you).
And my requests for additions:
Forsworn (yes please)
Witches (not sure if this one is applicable, but who knows)
Silver Hand (the werewolf hunters)
Caravan (this one, not sure of, you may need to make a new faction), for Khajiits.
GuruSR.


