here are things I considered

First, i really perfer a condo 'cause I am an adventurer, i absolutely need the washer/drying(we used it EVERYDAY) when i am hiking 12 miles a day in 85 degree, but if you only want to stroll on beach, hotel room is OK (Marriot Wailea is just beside Ekahi, very beautiful place and the "its" Ulua beach is super nice).Oh, the kitchen in condo is nice since dinning out is very expensive.

Second, you CAN get condo much cheaper in Kihei, BUT, Kihei is a very busy and ill planed (in my opinion) beach town: crowded, horrible traffic and dusty. The beach there are not good for swimming because of pollution (in Wailea, the seawater is so clean that it smells like fresh water). Also Tripadvisor.com has some posts about the bad/outdated condition of condos there. Maybe you can try Makena? it is less developed but its beaches are lovely and you might be the only one there... Or west maui (Kaanapali, Napili etc), it is definately more popular (crowded) but still better than Kihei...

Thirdly, I prefer condo close to beach to ones in the mountain because you can do sightseeing during the day and still have time to relax "at home" on beach. And where is the mountain you mentioned? I think one side of highway 310 is beach and the other side is "dryland"? ( they don;t have a lot of rain there)

Finally, Costco membership and GPS high recommended...

And you HAVE to go snorkeling, AMAZING experience

let me know if you have any questions, i got a lot of help from this board and I want to contribute too