Maui is still my favorite of the Hawaiian Islands. I agree that Wailea is a bit expensive for a RI-type of stay with Kihei being much easier (you'll probably spend time in Kihei anyway).

The condo recommendation at Kihei is definitely much better value than the category 8 points used in October, but to each their own. Looks like they charge for parking too at this RI.

I think it is very easy to occupy 5 nights in October.

First, a rental car is a MUST. If you are not a fan of driving, I don't think Maui works well.

Aside from the beach/sand time, just some of the things to think about include:

-Haleakala volcano (with all of the choices from driving, biking down, sunrise/sunset)
-High end/expensive dining in many places
-Doing a luau (with a guarantee that there will be timeshare sales at the RI to make this close to free)
-Farmers Market
-Farm plantation
-Many small and large parks including near the airport
-Hana (mostly the drive, but there are the pools and park at the end)
-Costco
-West Maui drive

There is also the Ocean Center, some ranches and other activities (including day trip to Lanai and other things that the tour companies come up with).

Rasheed