Aloha David,
Oahu RE investment is all about speculation. Trying to find MFs or single family homes with "Ohana units" to live "rent free" will be very hard to come by. You might be lucky if you're able to net a couple hundred dollars off a long term buy-and-hold if you purchase based off of cashflow in some cheaper areas. Where Oahu's investment strategy is strongest is in appreciation which is constantly trending skyward. Ex. 1984 SFH Median price was $158K now it's $690K. Believe me there are some grannys running around who became instant millionaires who bought a long time ago and recently sold.
If you plan to use your VA loan and have a budget below $$650K you'll be better off buying homes in the Central-Westside. If you can mange to buy something on East Oahu or Windward side would be the best option as appreciation and properties values are strongest there.
If you're looking to flip homes you'll need to focus on reaching off MLS deals/ buy with cash. 99% of properties listed on the MLS are at market value. The sooner you realize 75% of the value comes from the land a home is sitting on the better.
Constructing a home is an option but DEMO/Soil Engineering/Septic systems can be costly.
My advice is to get something when you arrive so you can take advantage of your VA loan while the rates are still good.
I would also think about getting a brand new Kakaako condo if you can (no VA loan/requires 20% down). This area is rapidly developing into a luxury/trendy/artsy neighborhood. Rents and property values are already taking off. There's a ton of cranes and construction in the area and as soon as the dust settles it'll be the hottest place to live in all of Hawaii. Kakaako rents property values will skyrocket as it becomes the neighborhood where anyone with $$$ will want to own. Visit ourkakaako.com for brief on the development.
Shoot me your email and I can get you more details! Aloha -Joe
