Traveling with kids might make it different, but I've always liked the idea of doing all the traveling in one day, and I think it's easier than when you have the overnight flight home. So last year and this year we fly in from the midwest (ORD or MSP) around 3PM and then connect to WP to JHM (Kapalua)...this way you're in before the night is over...get settled, get some dinner and go to bed early (since you're tired after 11+ hours of traveling). It's always seemed to us that less time is wasted. We connected through HNL from KOA on the way home last year, and thought it made the red eye a little rougher, so this year we are finishing on Oahu. Obviously a moot point if you fly home from OGG or KOA, but we've used awards, and I refuse to do the 757 to Hawaii!
That said, I think the most important thing is making all the interisland flights nonstop. We had to go JHM-HNL-ITO and that was a pain...so much wasted time. You think it will be easy because the flights are short, but it's a pain...that's why I like to do the connection after an 8h flight...at that point, waiting an hour for a 30min flight is no big deal!