My wife and I just returned yesterday from a 13 night trip to Hawaii where we celebrated our 25th wedding anniversary. We stayed 5 nights on Maui, 2 nights on the Big Island and 6 nights on Oahu at Aulani. I will be posting a (somewhat brief) TR by the end of this week, but you mention that you may be looking for an apartment in Maui near the beach for your family of 5, but your wife also loves adventure, so I wanted to suggest an alternative lodging which you might not come across in your research.
For our 5 nights on Maui, we stayed in the Starwind Cottage at the Maui Tradewinds (
http://www.mauitradewinds.com/StarWind.htm) and I couldn't possibly recommend the place any higher. It was ideal for our trip, but would also be a fabulous home base for a family wanting to explore Maui since it is centrally located in Haiku on the island's north shore only 10-15 minutes from Ho'okipa Beach (world-famous for wind surfing) and Baldwin Beach (totally NOT world-famous but an absolutely beautiful beach suitable for families - unless you stray too far to the east end away from the lifeguard station where clothing is optional!).
The Maui Tradewinds property consists of the main house where the owners (Bev and David) live, with a 'suite' on the bottom floor which is available for rent, and then a separate 'cottage' just in front of the main house (but very secluded with thick vegetation) which has a full kitchen, nice dining/living room, 2 bedrooms (each with a queen bed, but inflatable mattresses available so that the cottage accommodates up to 6 people). A full bathroom adjoins the 'master' bedroom but the 2nd bedroom has a half-bath plus a door leading outside to an outdoor shower so the cottage really functions as a full 2-bathroom unit. A beautiful deck (with immaculate hot tub!) spans the entire front of the cottage, with views of Haleakala in one direction and the 'distant' ocean in another direction. Both bedrooms have AC but the main living area does not (we used the AC when sleeping but the breezes during the day did not make us miss AC in the main living area). There is a washer/dryer on the bottom floor of the main house which is open 24/7 and is accessible for both the 'suite' and the cottage. It's literally 50 paces up the steep driveway. There is also a fridge outside the main house with extra beverages which you're welcome to take back to the cottage.
I hope I don't sound like a commercial but this place was absolutely perfect for us, and I can also envision that it would be perfect for a family of 4-5. We have 2 grown kids so we have lots of experience vacationing as a family and valuing accommodations with full kitchens, multiple bathrooms, flexible bedrooms, etc. We're DVC members for 20 years with BWV as our home resort and we always stay in 2BR units. Just as we value the location of the Boardwalk, we treasured the central location of Maui Tradewinds -- 25 minutes from the Kahului airport, 15 minutes to great north shore beaches, 1 hour to west Maui (Lahaina/Kaanapali), 1 hour to south Maui (Kehei/Wainea), 1 hour to Haleakala National Park entrance, 2 minutes to the Road to Hana (the unit is just off the main road but very secluded), and 20 minutes from the great 'upcountry' towns of Makawao and Kula.
If you're wife wants to be 'on the beach' in Maui then this won't work for you, but I strongly suggest you give it serious consideration. Also, they have a very relaxed reservation policy -- no money down, just a credit card to book and they charge your card upon check-in.
