let me save you the trouble and headache of 3yrs you'll want back.
Oahu when you first arrive is an amazing place. The culture, great weather and exciting/fun things to do suck you right in
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Visiting here for 2 or 3wks is going to make you fall in love with this place, you'll see. I've said it probably 1000 times, this place is AWESOME!!!!........... for vacation.
If you don't HAVE to live here, avoid it like the plague. Especially if you're a motorcyclist. This is the #1 motorcycle theft state in the country. yeah most of the bikes that are stolen are Jap bikes but there are Ducs and BMW's stolen too. As for your question, "wouldn't you see it on the island?" the answer is a hearty YES!!! but you can't do shit about it cause it's a giant conspiracy.... they all have clean paperwork within days of being stolen so once it's gone.... it's gone and you're assed out...... just pray you have gap insurance, if you don't.... GET IT!
As far as riding goes...... paint 2 walls.... one black and one white, stare at the white one for about 30min, then turn around and look at the black one for 30min, then turn around and look at the white one for 30min, after that, turn around and look at the black one for 30min..... you get the picture?? I think I heard somewhere you can ship your bike to Maui for like $130 one way... so $260 both ways, plus hotel costs and food and you're looking at probably about $1k for a whole weekend trip, yeah.... maybe once or twice a year.... then look at the white and black walls again.
As some others have said, jobs are everywhere you look, if you wanna work at L&L or something
. Bottom line there is that your wife will be the money maker so if I were you..... I'd find some internet type gig to make some side cash or something, that way you won't have to deal with the traffic. Speaking of traffic, most people HATE the traffic here and rightly so. Traffic is the same everywhere though, you don't move for like 3-5min, then you move about 3ft and wait again, that's just the nature of the beast. The real difference here is that they give licenses out to EVERYONE.... it seems there is not even an I.Q. requirement to operate a 4 wheeled vehicle here. as long as you know how to throw out the Shaka...... you're good to go.
This is also the most racist place I've witnessed.... against white people. but I guess we had that coming so whatever I can deal with it. Just don't go "exploring" the island after like 9pm and you'll be fine.
Living arrangements. If you can find a good safe place off base and save some cash, do it. I thought I could do it for a year and my bike got stolen and I didn't have gap insurance so..... yeah.... bye bye all the money I saved. On base peace of mind is worth every penny to me..... plus I know my house has AC and isn't "breezy" or "cozy". if you see those words in an ad... that means no AC and you're going to sweat your ballz off.
I'll throw out the disclaimer that I've been jaded here..... I've had a pretty bad experience overall but I will say that the first 6-9months I was here were GREAT!
If you love the beach life and wanna just "chill", you'll like it here. if you like to party and live it up in the clubs and night life, you'll enjoy your time. If you want to live your life, go on some good rides, save up some money, enjoy a variety of new experiences everyday and live with a populace that likes to abide by the laws/rules and not try to "screw" you at every turn out of some money...... this place is not for you.