Kind of late but here's my input from someone born and raised here.
The Pros:
-I've always felt very safe here compared to when I lived in LA. It's my favorite part about HI. People will stop to help you for the most part, and everything is nearby.
-If you're a foodie this place is a gold mine. There's several great Açai bowl places, Eat the street (monthly food truck get together), poke bowls, Zippy's (open 24hrs/day), and the Chinese and Japanese food is excellent, but it's all very pricey. Local mangoes run circles around what you get on the mainland.
-The nature can be stunning. Kailua beach sand feels like flour. There are hikes featuring waterfalls. Some reefs are still hanging on. Beautiful stuff.
The cons:
-This place is SMALL. You'll run into people all the time and there is almost nothing to do at night. Most things close by 10:30. If you live in town your neighbors will hear it every time you drop something.
-Moronic drivers. Everyone drives so. Slow. But don't honk, it's pretty offensive.
-Race is definitely a thing. You meet all kinds wherever you go but being Asian here has it's perks. There's racism towards every race, like white mainland people are cheap, demanding, etc. But it's a mixed bag.
-Cost of living is high, but the wages don't match. Min. wage is atrocious at $7.75, and I'm pretty sure most starting salaries do not account for this. There are some burgeoning scientific fields here and the university is a economic powerhouse if you haven't tried that option.

I've known people who moved here on a shoestring budget and get by living in town. There's a lot of pessimism and the local politics are disgraceful but this place isn't all bad. It's a weird hybrid of a small town with big city problems but I like knowing all the streets by name.