Hmmm....

If Aiona challenges Mike Gabbard, he'll be doing Gabbard a TREMENDOUS favor since the Hawaiian and environmental block is pretty pissed off at Gabbard (who is usually on the right side of these issues) giving in to pressure (I assume his chairmanship was at risk) and voting yes on HB2501 (the A&B water theft bill).  On hating gays they are same-same.

If he goes for the Mayor position, he's not going to get the major pushback from the environmentalists (just look at his opponents)

If he goes for CD1, he'll split the GOP vote and insure Hanabusa's win.

So IMO, his best chance is Mayor ( you can thank me later Oahu, LOL!)