We stayed at the Grand Wailea back in February. We used Lyft to get from the airport to the hotel, from the hotel to a grocery store and back, from the hotel to the Maui Ocean Center and our whale watching excursion and back. Our next to last day at the resort, we took a Lyft to the airport to pick up a rental car from Avis, which we used to explore "up country" (toward Haleakala) and the beginning of the Road to Hana. Our last night we relocated to the Marriott Courtyard by the airport to catch an early morning flight on Southwest. We had no trouble getting Lyft rides, all of the drivers were really nice and some were very entertaining. The resort also had a shuttle service available in the Wailea area, which we used to go to dinner a couple of times. This approach worked really well for us and I am confident that the Lyft rides were significantly less expensive than the combined cost of a rental car, gas, and the exorbinant parking charge at the hotel.
Some other tips:
Our favorite meal was at Matteo's Osteria in Wailea.
https://www.matteosmaui.com/We also really enjoyed Bistro Casanova in Kahului.
https://bistrocasanova.com/Our whale watching excursion with Triology was awesome.
https://sailtrilogy.com/ (I think October is too early for whales, but they offer other excursions)
The Maui Ocean Center was interesting and it is right across the street from the harbor where Trilogy is based.
https://mauioceancenter.com/