Wife and I stayed in a condo on Maalea Bay about 18 years ago, the central part of Maui on the west side. The wind blew very hard all the time with no storm anywhere near. You could hardly hold onto the car door when you opened it, and the cars all had dings on the sides from car doors getting away from people when they stepped out of the car. Wind surfing on the bay was a big thing, with the wind blowing non-stop all day.
It was long ago, but there were a good bit of debris on the road up to Lahaina, a few old stoves and refrigerators sitting out in grass on the sides of the road. Not a lot of development in the area from the mid-island up to Lahaina. It was late October and not overly crowded.
The trade winds are almost constant up in Kapalua north of Lahaina.
The best place to stay on Maui(IMHO)is Wailea or Makena.