Did you encourage Logan to go to the Bandit's Camp? Have you visited Caleb and had sex with him through the gloryhole? If you did both those things, just keep leaving the barn and going back. It doesn't cost any time on the game clock. If you did not do both those things it will not happen.
It isn't marked with a time-of-day requirement but I only ran one passthrough with Bottom Logan and it was after 19:00 if I remember correct.
The great thing about Bareshade is you can hop in and out of places, even the whole town, and as long as you don't interact the clock doesn't advance. I am persistent as hell when I want something RNG to trigger.