TLDR: Expert advice needed from house hacking investor and Hawaiian realtor!

I am moving to Oahu with my girlfriend and we want to take this opportunity to transition from renters to homeowners and from consumers to investors where through house hacking we would end each month cashflow positive. Or in other words, the rent received from house hacking would cover our housing costs (mortgage, property tax, insurance, repairs, utilities).

Upon research however Oahu seem to be a high cost and low cap rate area similar to SF where we currently live. I've struggled to find deals where a positive cash-on-cash return would be possible or even breakeven.

Expert advice needed

I am curious to hear from other investors what types of house hacking strategies has worked in Hawaii (or similar markets). 

Also I am looking for an experienced realtor on Oahu that has worked with investors and understand the investor mindset.

Type of house hacking strategies I am considering:

• Multiple units (duplex, multi family home)
• Single home with roommates (rent out extra bedrooms)
• Single home with vacation rental (Airbnb extra bedrooms)

And here are my criteria:

• Budget 60-75k downpayment
• Eastern windward side of Oahu (Kailua and surrounding neighborhoods)
• Renter or vacation goer friendly location
• Lightweight rehab (no fixer)

Aloha!

Marvin