This is the single most useful piece of advice about Dillingham and almost nobody follows it.
Skydiving and gliding here are cancelled by wind, cloud base and rain, and on this coast all three change within an hour. Operators do not fly outside their limits and will not be argued into it. If you book your jump for the morning of your flight home, a cancellation means you do not go.
Book the first bookable day of your trip. That gives you the rest of the week as rebooking window. Most operators will move you to another slot rather than refund, which only helps if you have days left.
Take the earliest slot of the day. Trade winds typically build through the morning and blow hardest in the afternoon, so the first loads are the most likely to fly and the least bumpy.
Expect to wait. Manifests run behind when a load is held for weather. Bring water and something to sit on; the passenger area is functional rather than comfortable, and there is no café.
Allow half a day including the drive. From Waikīkī it is an hour each way before anything happens, and hotel pickup services stretch that considerably.
Confirm the morning of. Call. Do not drive an hour on the assumption that a booking made three weeks ago is still flying today.