January is a good time to move from D.C. to Hawaii.

If you fly to the U.S. mainland a lot then UA will serve you well with many flights a day. However, the HNL-ORD flight is being discontinued in Feb so that will add at least one more connection on the west coast to fly anywhere in the east.

I've had good experiences flying to Asia on UA too except that many places need a long layover in Narita.

Your major problem is that there are a lot of Premier members in Hawaii (all those trips to Las Vegas). This could reduce your chances for an upgrade. On the plus side, you can use all those upgrade certificates for travel to/from Hawaii when you become a HI resident.