For this property, the boiler went out (cost $25,000, is what I told you in the past), and the pipes burst, damaging the ceiling and surrounding area.

That's a good idea to look at surrounding well performing properties and replicate. 

Surrounding similar lots have been redeveloped into $2-3M homes.I obviously need to rehab/build a house on it to bring the value up to its potential, but I'm not sure where to start with this?

A+ area which has appreciated 1-2% percent more than surrounding areas over the past 5 years.

@Andrew SwaimHey Andrew,  Id be happy to chat about what you're looking for, I'm a full time investor in Virginia Beach and surrounding regionSent you a message 

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 downpaymentEastern windward side of Oahu (Kailua and surrounding neighborhoods)Renter or vacation goer friendly locationLightweight rehab (no fixer)Aloha!

Land Constraints: - Surrounded by dense mountains, our small market only measures about 15x20 miles. - Lots of demand from Northern California, and not a lot of supply. 2.

Continue to surround yourself with other investors and you will be amazed at how much you can learn and progress through out your real estate journey.

The surrounding counties aren't as bad, talking with local attorneys and investors.

You'd also be surrounded by (granted they are SFH) 30-60k homes.