It was our first time on Maui so I wanted to see as much as I could. Kihei was fine as a home base and probably cheaper than the resort areas in Kaanapali and Wailea. If I had the cash and just wanted to show up and not move around a lot I’d probably stay in one of those places.
If you want to drive around a bit Kihei is probably a good choice. Just understand your probably going to drive 20-45 minutes to some of the nicer beaches.
Also download the Gypsy guide app. It’s a GPS guide that gives navigation directions and tells stories as you drive. We learned a lot about the history of Hawaii as we drove around, especially on the road to Hana.
As for the Road to Hana, we did it the “back way” going south through the back country and then east across the south part of the island. It was a cool drive with very little traffic but sketchy in a few places. But I never felt unsafe. I liked going this way because we got to some of the cooler places on the road to Hana first in the day whereas most people get to those later. Road to Hana is a long day but worth it. Do the Oheo Gulch hike. It’s 4 miles round trip but there’s an awesome bamboo first and great waterfall payoff at the end. Hamoa Beach was probably our favorite beach of all we went to on the island.