So a wild theory I have after watching Chucky Season 3 Episode 2...
What if the woman that was in those photos with President Collins was one of two women:
Tiffany (which would explain Chucky having a link to the family)
Lexi's Mom (Which would add to the hesitancy of Mrs. Collins letting the trio hang out with her son)
Because (and correct me if I'm wrong) the woman in those photos was a blonde, so those two are my immediate first guesses.