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How exactly are you defining city? Because to someone from Littleton, CO, oh my goodness was Honolulu a big busy and crowded place! Also, will you have a car, or will you need to rely on public transportation? Honolulu is the only "city" per se in Hawaii, although as hotzcatz said, there are many towns. I recommend you stick to the touristy areas, although you could probably find some affordably housing up near manoa, kaimuki area. public transportation on oahu is excellent- although you should get a monthly bus pass. Kailua is very pretty, but is by no means a "city" like you may be used to and commuting from one side of the island to the other is a bit of a headache (think massive traffic).
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