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Do not assume every Hawaii listing gives you the same ownership interest. A fee-simple purchase generally includes ownership of the land and improvements associated with the property. A leasehold purchase involves acquiring an interest in the improvements or property while the underlying land remains subject to a lease.

If you are considering leasehold property, review the remaining lease term, lease rent, future rent-reset provisions, financing requirements, transfer provisions and what happens when the lease approaches expiration. The distinction can even affect financing programs: HHFDC's current Hale Kamaʻāina program requires an eligible leasehold property to have at least 35 years remaining on the lease and fixed lease rent for at least 10 years from the mortgage date.

Condominium due diligence deserves more than a quick look at the monthly maintenance fee. Hawaii's Real Estate Branch maintains resources specifically for prospective condominium buyers, including Developer's Public Reports and information on associations, governance, finances, reserves, insurance and owner responsibilities.

Before committing, review association budgets and financial statements, reserve funding and recent reserve studies, pending or recent special assessments, master insurance coverage, maintenance-fee history, governing documents and house rules, major planned repairs or capital projects, disclosed litigation or material association issues, and any leasehold terms affecting the unit or project. DCCA warns that inadequate condominium reserves can ultimately result in special assessments, borrowing or delayed repairs.

The Hawaiʻi Emergency Management Agency notes that different policies cover different hazards and specifically points homeowners toward potential fire, hurricane, flood, earthquake and lava-flow coverage depending on the property.

It also cautions that coverage varies by policy. Hurricane wind coverage and flood-related damage, for example, are not necessarily handled by the same insurance. Ask about insurability and expected premiums early enough that the answer can inform your purchase decision.

Real property taxation and homeowner exemptions are administered at the county level in Hawaii, so do not assume the same classification or exemption rules apply on every island.

Hawaii also has a state conveyance-tax system associated with transfers of real property. Rates and transaction treatment can change, so confirm current figures with your escrow professional, tax professional or other qualified adviser instead of relying on an old online estimate.