A few things I am thinking about...
1.22 What causes the simple to love simplicity? How do we position them to "see the light" and wise up?
1.23 What is the correct response of a parent to a child who hates knowledge (What kind of knowledge is it talking about here? Book learning, Bible verses, or something more related to 1.4 and 1.7 where it is associated with discretion and the fear of the Lord with and wisdom and instruction). There is a hint in verse 23.
1.28 How do we teach our children that life is not an endless stream of second, third, fourth, etc. chances?
1.29 "Choose" is an important word for children. As parents our responsibility is not to give our children choices but teach the to discern and choose the right way, the fear of the Lord. How do you teach your children to make good choices?
1.32a and 33a What is being contrasted in 32b with turning away 1.32b and 33b What is the difference between complacency and safety? How can our children tell which one they have?
(also Proverbs 1:4; Proverbs 1:7; Proverbs 1:29; Proverbs 2:5-6; Proverbs 2:10; Proverbs 3:20; Proverbs 8:10; Proverbs 8:12; Proverbs 9:10; Proverbs 10:14; Proverbs 11:9; Proverbs 12:1; Proverbs 12:23; Proverbs 13:16; Proverbs 14:6; Proverbs 15:2; Proverbs 15:7; Proverbs 15:14; Proverbs 17:27; Proverbs 18:15; Proverbs 19:2; Proverbs 20:15; Proverbs 22:12; Proverbs 24:4-5; Proverbs 29:7; Proverbs 30:3).