I don't live there (yet), but rented a one bedroom place in a residential neighborhood of Kihei for just under two weeks to get the experience and analyze this. Its on my consideration list, especially if we have kids and when they get near school-age and have to settle down and set roots somewhere. I like Maui because its a bit more developed (and probably less isolating) than the Big Island or Kauai, but is not the urban sprawl and expense of Oahu.
Here's my analysis:
- Housing is the biggest expense, $800,000 will get you a nice, newer 3bd, 1500sqft home. "Average" house prices are a little overstated because many of those include an Ohana or part of the home that gets rented out. If you're willing to deal with being a short-term landlord or sharing a portion of your property, the housing cost can drop.
- Refrigerated/Frozen Food items probably come next in cost. If it 1) Has to come from the mainland and 2) Requires refrigeration/freezing, its extremely expensive. Outside of that, I didn't find food to be all that expensive. Kihei has a Safeway and many of the prices (outside of refrigerated/frozen food produced on the mainland) were not all that different than our Safeway in Dallas. They also ran the loss leader sales. Costco seemed to be the same price as Dallas + the cost to ship. So lightweight/small items were barely noticeable on price, heavy/bulky items cost more. Adjust your diet accordingly.
- Fuel/Electricity is more expensive, it all gets brought in by tankers. Costco wins again for gasoline. You then have to be okay with a temperature that moves around, if you want to A/C your house to 68 degrees all the time, live in Arizona. Most people had shaded areas outdoors they used and windows on all four sides of the house. We were staying probably 50ft above sea level, some of the most popular housing developments in that area were a couple hundred feet up with more wind exposure.
- Travel back to the mainland will be costly. Maui is a little better than the Big Island or Kauai in that it has more flights direct to the mainland vs. having to pay Hawaiian air to take you to Honolulu then fly back. Travel hack for airlines miles. Maui has direct flights into DFW and American miles are one of the easiest to accumulate.
- You always have the option to go do something part-time, there are lots of lowish-paying tourism gigs that'll hire you if you can speak professionally to someone and show up on time. Its amazing how much $10,000 or $15,000 in earned income can tilt the cost of living analysis.
I hope that helps.