I know what you're saying, but I also feel that one needs to consider the perspectives. Like they say, grass is greener. He was just not into Hawaii, and I don't think there is anything wrong with that. Personally, I hated living in the SF Bay Area. It was just not for me either. I know, I know. People think I'm nuts. But, after 10 years of living there, I finally understood my math professor. I was like, "Wow, I can't imagine professor Lady going through something like what I'm going through for over 30 years!" I really felt for him. By the time I finally left the Bay Area, I was utterly burnt out by big city, fast paced life. It made me the person who I am today: one foot out the door at all times. My wife and I moved around several times in the years since, and now that we're back in California living in a smaller coastal city, I realized what I hated about being in the Bay Area: it's just too big, too much of a rat race. Although I love living where we're at now, I can eventually see myself growing tired of it.
And, that's the perspective, I think, you're missing out on. You are seeing things from your own perspective. I know that perspective well, too. I lived it for 10 years. I was a techie; I was always wary of being laid off; I had crap for vacations; I was ALWAYS learning new stuff; and as techies, we're always crapped on. I had business envy and thought of going to business school. So, I see your perspective. But, I also see his.
Being in Hawaii, or any other small town/city, can get very old and tiresome. Several of the Hawaii math professors eventually gave up tenure and moved away to do other things. It makes one wonder about why these guys would be willing to give up a highly sought after thing in academia, tenure, to move away and start a new life. I think my old professor provides a good explanation, at least for some people, about why that happens. At least, it did for me.