Investment vs. Lifestyle: Why People Really Buy in Hawaii

Many buyers call me saying they want to invest in a property here. What they usually mean is they’re looking for a short-term vacation rental — something that can generate income when they’re not using it. They’ll often say, “I don’t just want it to cover expenses, I want it to cash flow.”

To help with that, I’m always happy to put together a proforma on any property. That includes all the expenses, projected revenue, property management fees, taxes, and more. Once buyers see the net income number, they sometimes realize the property may not cash flow, especially if they’re financing it with a loan. That’s just the reality.

At that point, many say, “Well, I could do better investing in the Stock Market or somewhere else.” And yes — that’s absolutely true. But here’s the thing: you’re not buying in Hawaii just for the investment. You’re buying for the lifestyle.

The Lifestyle Factor

It’s 84°, the surf is up, and the sky is beautiful. That’s the lifestyle you’re buying into.

  • I play pickleball outdoors two or three times a week — year-round.
  • I golf at some of the most spectacular courses in the country.
  • I head to the beach on an Aloha Friday afternoon to grab a poke bowl and watch the waves.
  • We boogie board, surf, or simply relax on some of the world’s best beaches.

You can’t do any of that with the S&P 500. You might get a higher return there, but it won’t give you priceless memories with family and friends in paradise.

The Big Question

So ask yourself: do you really need a property that maximizes returns — or do you want something that helps cover costs while fueling your dream lifestyle?

And here’s the bigger question: what’s holding you back from starting your Hawaiian lifestyle right now?

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