Drop all checked bags. Don't stop off bags you want or need to stay with you (those containing medicine, ID to board the ship, etc). And yes you totally can. Wish more people would, as it would speed up the shuttle process.
But knowing that you don't like dealing luggage is a good first step in this decision.
There's rarely a time on vacation when one has to deal with their own luggage, apart from packing and unpacking it. Just up the tip budget and ask for assistance.
At the airport hire porters to follow you to the rental car if you go that route. Drop off at the port with those porters. On the way back, reverse it.
Dh and I are strong, capable people, but when I've funded the tip bidder appropriately we enjoy just outsourcing the luggage handling aspect of a trip.
Car service works nicely too. Ask if they meet you and take your bags.
And consider doing laundry on your trip. It can cut down on all you need to take. You mentioned aulani so I wonder if you own dvc. If so, laundry's free at the WDW dvc resorts. Can be a nice little break from the go-go-go.