I'm also stuck on the Waiting part of The Blind Hunt -.-' Been waiting around for over 2 game weeks with talking with her nearly everyday, asking Hopes and Dreams, romanced her once, haven't collared her or anything like that. Made a separate save and released her but no POI in Westside, freed her slavery and released but no POI. Idk what else to do... max her Affection? Decrease her Willpower? Get her pregnant? Fight her traits and raise her Corruption?? The Wiki and other info have been frustratingly vague -.-'
Ok, I finally found out how - Just talk to her first thing in the morning and that *should* progress you past the Waiting part of Caitlin's Blind Hunt quest. Hope it helps!