I live on Oahu too - ride right through Waikiki on every ride - usually by 3:00 AM.
I've had trouble with the rain too, of course. I managed to get a ride in Wednesday and another last Sunday, but since I normally ride every other day, that is below par.
I'll try again Saturday morning, but the forecast isn't too good.
As for shoes, I just use the Shimano sandals and don't worry about getting them wet.
Bob