My personal opinion, but I think no matter who is selected, even if they believe in CCW would never buck a system they are part of. Without some major legal action I don't see the CCW policy changing anytime soon.
I do hear what you're saying, but I think it's different for the Chief of Police. With HPD, he's not part of the system, he
is the system. If he's pro-2a, the department will be pro-2a. That might end up with the police commissioners replacing him, but honestly, who cares? He's at the apex of his career right now with HPD, the only way to go higher is either to seek elected office here in Hawaii, or pursue a C.O.P. job elsewhere with a bigger, more prestigious department, and there are a number of cities in the US that would look favorably on a guy who was willing to risk his job to do what's right for his citizens.
Bottom line is, HPD as an organization is just like a ship or infantry unit; they all reflect the personality and disposition of their commanding officer.
Edit to add that it's not like we're expecting him to engage in civil disobedience or anything; in this case, "bucking the system" means acting within the lawful bounds of his office in a manner that may be unpopular.