What Makes a Great Long-Term Rental Property?

A Checklist for Smart Investors in Maui
01 Sep 2025 – by Terry Craven

Real estate continues to dominate as America’s favorite long-term investment strategy. For the 12th consecutive year, 37% of Americans consider real estate the top investment choice—nearly doubling stocks at just 16%. This isn’t just sentiment; investors are putting their money where their beliefs are, purchasing 13% of all homes sold in 2024.

The truth is, real estate offers unique advantages that traditional investments can’t match. A rental property provides multiple income streams, delivering monthly rent payments while simultaneously building equity and appreciating in value. Leverage amplifies returns: Even if you put down 20%, you’ll benefit from 100% of the property’s appreciation gains. Tax advantages, such as depreciation and deductible expenses, can further boost profitability.

When done wisely—and with the right local management—rental properties can deliver steady cash flow today and significant wealth tomorrow.

How Rental Properties Build Wealth

Great rental properties create wealth through three primary channels that work together to compound returns over time:

• Cash Flow: Net monthly income after expenses (mortgage, taxes, insurance, maintenance, management fees, etc.).
• Appreciation: Value increases over time. Historically, U.S. home prices have risen approximately 3–5% annually.
• Equity Growth: Loan principal reduction as tenants’ rent covers mortgage payments.

The total return combines all three. While individual components might not create overnight wealth, together they compound impressively for patient investors.

Who Should Invest in Rentals?

Rental property investing rewards long-term thinkers who are financially stable and patient. Strong down payments and cash reserves are essential, as real estate is illiquid and comes with unexpected challenges.

But in Maui, success also requires professional, on-island property management. Hawai‘i law mandates that all rental properties—whether short-term vacation rentals or long-term leases—must have an on-island property manager or agent who can respond promptly to tenant and property issues.

That’s where I come in: as your Maui-based broker and property manager, I safeguard your investment, handle tenant relations, oversee maintenance, and ensure your property stays compliant with local laws while generating reliable income.

Where to Begin Your Investment Journey

The first step is to connect with a real estate professional who understands investment property in Maui. I provide:

• Exclusive Access: Insight into opportunities and off-market listings.
• Local Market Expertise: Knowledge of which neighborhoods, property types, and features perform best with renters.
• Financial Preparation Support: I’ll help you gather the key numbers—such as expected rent ranges, typical expenses, HOA fees, and insurance estimates—so you can review them with your CPA or financial advisor.
• Full-Service Management: From tenant screening to maintenance and compliance, I handle the essentials so your property generates income stress-free.

Your Rental Property Evaluation Checklist

Smart investors use a systematic approach to identify great opportunities. With my guidance, we evaluate properties using:

☑ Location & Market Analysis – Demand, vacancy rates, schools, safety, and local growth trends.
☑ Financial Preparation – I assist in collecting and organizing financial data for each potential property. You’ll then review these numbers with your CPA or financial advisor to determine profitability.
☑ Property Condition – Professional inspections to avoid costly surprises.
☑ Property Type – Properties with the best rental appeal in Maui’s market.
☑ Due Diligence – Verified numbers, legal compliance, and alignment with Hawai‘i landlord-tenant law.

This checklist ensures we avoid costly mistakes and identify the properties with the strongest long-term potential.

Bottom Line

Great rental properties aren’t found by chance—they’re identified through careful evaluation and managed by professionals who understand both the market and the law.

In Maui, investors must have an on-island manager for short-term rentals and an on-island agent or contact for long-term rentals. My role is to ensure your property not only complies but thrives. With patience, proper preparation, and the right team, your real estate investment can generate steady income today while building lasting wealth for tomorrow.

Ready to start building your Maui real estate portfolio? Let’s discuss how these principles apply to the best opportunities available right now.