plenty of accomodation in Kahalui, give Suzie and Dave a call at Action Sports, they have heaps of good contacts as well,

You will get slugged $100 each way from honolulu to Maui, flying with Hawaiian

Should be OK on Jetstar with surf board, we carry full windsurfing rigs in bags, never been too big an issue

Food, where to start, Paia has the best options in my opinion, but great ribs at the Ale house Kahalui, also good lunch options at Whole foods (Actially everything is good at whole foods!)

Cheap cars from Al West

Can you use your 9m kite in 35 knot winds?

Go see 1. Haleakala 2. Hana Highway 3. La Perouse coast is amazing, keep an eye out for south swells if you taking your surf board. 4. buy a snorkel and hit the reefs before it gets windy, amazing......also head up to Waihee waterfall and dam system, cool jumping spots.

Above all respect the locals, learn to shaka and smile

If you dont mind driving and want to stay away from the north shore give Kihei a go.
Some very nice condo's all along Sth Kihei Rd.
If you want something schmick then give Maui Sunset a go.
Nice accom with beautiful grounds, pool etc. Walking distance to some great restaurants and bars.
Its about a 20 minute drive to Kanaha, Sprecks etc.