Hi Jeremy,
At your level, Oahu is the only real choice. You need Kailua Bay it is usually a steady 15-18 knots trade wind, which blows non stop between May and October. Maui tends to be crowded, gusty and strong.
You dont want to stay in Waikiki, look for private accomodation rental on the net. Anywhere in Kailua or Lanikai is good. Not much night life but if you want to practice your kiting, it's the sh1t!
Good winds,