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I've done quite a few weekend trips using Island Air when it flew to JHM and I've done quite a few weekend and buisness trips that required me to fly into OGG and drive to Kapalua. I'd give a slight edge toward flying into JHM. Traffic from OGG to Kaanapali can be bad at certain times of day but you do miss out on a very scenic drive (just don't drive 20 mph because you want to snap a picture). Otoh, there are less flight options out of JHM, especially right now until Ohana starts up.

I have seen the Kapalua resorts shuttle at JHM for pick up. Believe the WKORV has a shuttle too (or at least it did a few years ago). Unless you want to be stuck at the resort though, it's probably best to rent a car. There are some great snorkeling spots (Napili, Honolua, etc) around Kaanapli that should not be missed.