Video letter is from a woman whose friend has a precocious 9yo son. He's an obnoxious manipulative boor. I say, when he behaves badly to you, leave.
Prudie compares the kid to Stewie Griffin and suggests seeing her BFF without the kid.
Letter 3 is from a crazy lesbian who is letting her girlfriend influence her with regard to LW's "relationship" with her crazy, racist, homophobic estranged father. I say: tell the GF to stuff it. This biological sample donor was not part of your life for some 20 years, and won't ever be a part of your life. Period.
Letter 4 is from a well-educated dummy who wonders if the low-income applicant to his alma mater is really low income. That, dear sir, is the role of the financial aid procedure, not amateur google-detectives.