1. i don't know for sure on this one since i quit playing Oldrim a long time ago. Maybe JD knows more about this. Anyway i don't think it's a big issue here 2. is a known game bug. Can be fixed by reloading an earlier save, and prior to entering the Drunken Huntsman, commit a minor crime in front of a Whiterun guard which causes you to gain a bounty, then clear that bounty. This may also work if you have already triggered his hostility, but have not been attacked by the guards.