Got both of the conditions, does the time matter? gonna try again
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.