I ended up ordering a basic 1 speed Electra cruiser (the mint color I wanted was out of stock). The people at the LBS were really helpful, and I'll have free access to their air pump as well as a first free tune-up. What a difference when comparing with the less than helpful customer service at the Department store!
I should also be able to sell it and get a decent price when I leave Hawaii. If I shell out for a more expensive U lock and register it, they will replace the bike if someone breaks the lock and steals it.
I'm thinking of adding a front basket for carrying beach stuff, but Electra's own were at least 30 bucks
My bike should get here in less than two weeks, I can't wait to start cruising again!
Thanks again for the advice everyone, here's hoping I made the right choice!