So it seems like you can build friendship with Logan, even after he has turned into a big old bottom, if your stop by the sawmill and talk to him. Seems like if your strength is high enough an option pops up and you help out without asking.
Seems like you can do it once a day and it builds 2 or 3 points.
So now I don't have to help Bernie at the shop and pray Logan shows up.
So now my routine is
Wake up, go to town, help out Logan, help out Bernie, help out at Hot spring, offer services at shop, do jobs at Tavern, and go to bed somewhere.
With occasional banging with various peoples.