We will be splitting our stay between Wailea and Kaanapali. Which would be better to go to Haleakala from, or are they about the same drive time?

Is sunrise better than sunset? I am thinking I'd rather go at sunset, but is it that much better for sunrise?

Wailea is about 15 or 20 minutes closer to the road to Haleakala.

We were staying in Lahaina and drove up mid-morning. My family didn't want to get up in the middle of the night to do sunrise. Haleakala is spectacular and not to be missed. Sorry don't know which is the easier drive, and I think the time of day is just personal choice.

Wailea is a better home base for sightseeing Haleakala and Upcountry, Road to Hana and Iao Valley. You'll have four-lane highway all the way back to Kahului. The only access to West Maui is via a two-lane connector between Maalaea and Lahaina. It takes me about 40 minutes between Wailea and Lahaina in good traffic; avoid rush hours when the 'worker bees' are commuting.

If you are interested in hiking into the crater, you'd go for sunrise or during the day. Halealaka is interesting all day, and you can run into cloud cover at any time.

Go up (I agree, from Wailea) while the sun is shining, enjoy the many microclimates on the way, then the awesome views from the top and the colors of the crater, then stay on one of the many west-facing pullouts for the sunset (bring a sack meal). The view from above the clouds is simply stunning, and the sunset colors breathtaking.
Driving up a strange road in the dark of the night, to watch an overcast (4 times for me) sky lightening in frigid conditions is frankly a lousy experience. (Then there's the fun "play dodge the bikes" on the descent.)
Going up in the daytime, enjoying the place, then the sunset, is far more rewarding! IMO

Thank you!

If you are coming from the east coast of the US, jet lag often makes it easy to wake up in the middle of the night. I've been to the sunrise twice. Once, the sugar cane fields were burning (apparently this is done on purpose regularly) and the sight at night was really something.

One thing to keep in mind if you do go at night -- it's 10,000 feet and it's cold. Bring a jacket or a blanket.

Even if you go during the day, it is COLD up there!

Yes, temps are usually in the 60s at the summit, but it can be quite windy, and so feel cooler.