It seems that the more complicated itineraries may require a call to HA to make the reservations. Unfortunately, that may incur a phone reservation fee. Have you tried one of the booking sites (travelocity or expedia). Their booking engines may be more sophisticated than HA's website.
While I find HA's flight attendants friendly and the Hawaiian-themed atmosphere on the plane soothing, I'm not sure if HA's service is going to be overly impressive. It's probably better than other US carriers, but may not be as good as some Asian carriers.