Yes you can - Oahu isn’t THAT small. But your larger point is correct - you can’t drive 100 miles there.
Cost of living is definitely an issue but it kind of depends on where you are in life. As a home-owning retiree with no children at home, I don’t find it particularly costly. There are no heating bills, recreation is free if you like the out-of-doors (I do), and you don’t have to spend much on clothing since the dress code is much more casual (and no winter coats). People drive their cars for many years if they need to, since weather and road conditions don’t do a lot of damage.
But if you have children to educate and you need to pay rent or a mortgage, and heaven forbid you have multiple relatives on the mainland you’d like to see occasionally - then the cost of living is going to be much higher.
As for me, I dislike Honolulu. It may not be huge by US city standards, but it’s got a big-city vibe, by which I mean you can go for blocks and blocks and blocks seeing nothing but asphalt and skyscrapers (I exaggerate, but only a little - your feet won’t touch grass if you are walking a couple of miles from your apartment to your favorite restaurant. UGH.)
Where I live (Hawai’i Island, aka Big Island) is not for everyone, but I love it here. I have beautiful views of palm trees and ocean all around me. I’m never bone-achingly cold (chilly sometimes, but that’s bearable). My breakfast this morning included papaya with lime, all from fruit we grew right here on our own land. People are pretty darn nice - the “aloha spirit” can be over-romanticized, but it really is real.
I understand feeling trapped by an island, but having spent decades living all over the world, I’m quite happy to plop myself down here and not travel much. So it works for me.
It may also help to live on the leeward side of the island in question (i.e. away from the trade winds), because the rain imbalance from one side to the other is often stark.
60% of the US population (and I bet a good chunk of Canada’s) is within a half day’s drive to Ohio, where I live.
I don’t think being on an island that is a 5 hour flight from the west coast of the US is something I’d be in to. I like being in “the heart of it all.”
I checked. The straight line distance from Honolulu to Kawela Bay (the furthest point away on Oahu) is twenty-seven miles. But I see there is no road along this direct route; the shortest driving distance is thirty-nine miles.
It appears that the longest drive you can take on Oahu, without intentionally going out of your way, is the 58.4 mile drive from Alan Davis Beach on one end of the island to Kaʻena Point State Park which is on the opposite end.
Here’s a bit of Oahu driving trivia. The driving distance from Alan Davis Beach to Ka’ena Point Trailhead is only 50.4 miles. The Ka’ena Point Trailhead and the entrance to Ka’ena Point State Park are connected by a hiking trail that looks to be about a mile and a half long - but there’s no road connecting these two locations. To drive from Ka’ena Point Trailhead to Ka’ena Point State Park is a fifty-five mile drive.
I live in SoCal- in fact I have lived here all my life (the Government has sent me to other states on a detail, and I have visited Canada (relatives) and Mexico). No humidity. Yes, it gets 100 degrees in two summer months. But “it’s a dry heat”… I visited Texas, Alabama, Hawaii, and Florida- the humidity and heat is not livable IMHO. Here, chaparral, at nite the temps drop way down at nite so we turn off the AC and open the windows.
“Dry heat” stay in the shade, and stay hydrated- and you are fine.
Now, I was stationed for one week (or was it two?) in the middle of Downtown Honolulu, so maybe I did not see the islands at their best- but the AC was on all nite. I wouldn’t mind going back on vacation, mind you- that Disney resort looks nice.
I remember our per diem barely covered our meals, but I admit the GSA is pretty cheap-ass. Thank gawd we had free lunches in the training center most days.
Wife and I visited the islands 2 years ago. Honestly I was like ‘Meh’ Quite underwhelmed.
The costs where not a shock, but I already live in a tourist area, so I’m used to that. I’m not really a beach/water person though. I did used to SCBA dive, but that’s different, and I don’t dive anymore.
I have actually been considering a move to Honolulu, somewhat missing island life and always having wanted to go to Hawaii. I even have a remote job that permits me to work from any place in the United States that I want. The problem is that my salary is <$60k and it would be tough to eke out a living in Honolulu on that pay. I’d have to find a second income source.
But - having never yet set foot in Hawaii yet in my life, I won’t do it without at least 2-3 visits to Honolulu first.
I know I wouldn’t like living in Honolulu. Too many people, too many tourists, and the high cost of everything.
A lot of small islands are like this, too. I live in Ohio, and would never want to live on Put-in-Bay or Macinac Island, for the same reasons. But not all islands are like that. Earlier this year my wife and I drove around Manitoulin Island. That’s an island I could live on. Plus there’s a bridge to the mainland, which is nice.
I actually had the opportunity to be stationed in Hawaii (at Pearl Harbor) when I was in the Navy. I declined for the following reasons:
Cost of living
I heard the natives resent outsiders who live there.
I was told being on an island gets old sooner than you think.
I was single at the time and would be an 8+ hour plane flight away from family.
Decades later I finally went there to visit. It was very nice visiting as a tourist. We spent three nights in Maui, three nights on the Big Island, and seven nights on Oahu. But after just a week staying on Oahu, I started feeling seriously claustrophobic. It didn’t help that we had two instances of having to backtrack for 1-1/2 hours because of a closed road. If the ring road on the coast is closed for whatever reason, there is typically no place to go other than back around the island the other way.
(Currently, we’re two minutes away if we walk.)