Welcome aboard Moose, there’s a seat for you down front and the lounge and snacks are straight back.
I’m going to come down on the side of - not worth the aggravation and headache. Hawaii typically has high non-rev loads, add to that June (peak season for weddings/honeymoons and family travel) plus 5 people on buddy passes with only 1 day of leeway - it has (Black Hole) days in the airport written all over it.

My suggestion, non-rev to LAX/SFO and purchase tickets onward. Both HA and WN have periodic airfare deals from the west coast to Hawaii. Go on their sites and sign up for special deals.