Is one guaranteed Jannah if ones infant has past away?

As Salaamu Alaikum

1) If you lose your child when they are very young (3 months old), are you guaranteed Jannah since they will take you there?

2) A family member uses her lost husband and her lost child (at 3 months) as a justification to gamble in the casino. Her other children are alive and doing well. This habit is incurable and our attempts to stop her has failed. What can be done?
Jazakallah