This is what I would likely do, another thing to remember is that each round-trip ticket purchased using points will have a $11.60 TSA fee that would need to be paid.


So my suggestion - purchase your own ticket with Gift Card $ (more points towards you possibly reaching A-List or Companion Pass) and get the families tickets using your points.

This also avoids needing to manage multiple family members Southwest accounts and remembering how many points are in each one.