what are you plannig for the next update?
Do the following things to get to them when you have it ready to unlock: 1. talk with the bartender about the cocky guard (He is in the Tavern, which you can enter between 21:00 to 5:55, if you have trouble trying to get a list of topics you can have him talk about, select rumors after using the talk option)
2. see Scar's event on the tracks (This can happen at night, so between 21:00 to 5:55)
3. Talk to Jester about entering the camp outside of night time (If you sneak in the camp at night, you might run into him which should unlock the talk option for him during night time)
4. You should be able to sneak into camp during the day (This is when you can start the boss fight against those 2)
Also, you need to sort out the situation where Logan either stay in town or head to the bandit camp.
The part where you can go and attack the camp during the day can only be talked about at night, and i think i know why your not getting any new chat choices with him, you need to clear the quests where you give him 10 Meat and 15 Beer first, it should unlock the new talk option from him when chatting with him during the night.