Definitely book where you'll camp or park WAY in advance. It is illegal to sleep on the side of the road.
Our initial plans were to book a hotel. Once we realized the cost, we were grateful for a 4-wheeled hotel that we could travel with.
Christine was great to work and communicate with. And I enjoyed seeing so much more of the island than we would have otherwise.
The first night was rough because we didn't book a place to sleep in advance. But we enjoyed every night after that and feel like we got much more of the Maui experience than if we were geo-locked into a single dwelling.
I wish I would have known upon booking that parking/camping would be close to $70 a night, so please keep that in mind.
We'd definitely book with Christine again in the future--but we'll probably take the kids next time so we'd need something bigger unless we rent a car and tent camp.