Welcome to FT.

Depends. First pick the airline that flies most often when and where you want to go. Then go to its forum on FT and search for challenges. try a challenge for fast status.

Flying from Hawaii, my guess is that your average trip will entail a lot of miles unless you are just island hopping. So getting miles vs. segments ought not be a major issue. If you don't find a good challenge program, call the airline and ask it to make you an offer.

Good luck.