This seems to be a rather inefficient way to book the airfare for this trip.

You can book something like this as a single United award:

ROC-ORD-SFO (stopover)
SFO-OGG (destination)
open jaw between OGG and ITO - you can probably find a cheap flight in cash
ITO-LAX-ORD-ROC

For 40k miles in coach plus $10. That's a single UA card signup.

This works because United allows one stopover and two open jaws per award to Hawaii.

For the OGG-ITO flight, theoretically you could book that using an extra 5000 United miles on a Hawaiian air flight. Not sure if it would be valid to add that to the main ticket (i.e. book everything as a single ticket at 45000 miles) or if you would have to book that separately. Either way, you get the entire vacation at one signup per person.

Everything is subject to availability but you're booking way in advance, which helps.