Oahu Buy and Hold

[Jonathan Paz]

I'm an active duty Air Force member moving to Hawaii in a couple of months and wanted to see if anyone has any tips for buy and hold. I will be working at JB Hickam/Pearl Harbor and my wife will be working at Wheeler Army Airfield. First, location is important to us, as we really do not want to deal with a lot of traffic and we also would like to be in a good neighborhood. We were thinking that living closer to Hickam would be good as traffic for my wife to go to/from work at Wheeler wouldn't be that bad as since it's opposite from Honolulu. Second, I'm a buy and hold investor looking to retire on real estate. Is there a strategy that works best on Hawaii, such as a "cheap" vacation condos versus a multi-family? It seems impossible to cash flow positive on a standard SFR so that is basically out of the question unless it has some additional living quarters that can be converted/rented out. Also, Hawaii seems to have a lot of strict rental restrictions and there seems to be very limited communities that are pet friends (I have a 60lb lab). I have VA Loan eligibility which allows me to buy up to a 4-plex with 0 down. Thoughts? Maybe just find a place to rent for cheaper than buying and use my extra money to invest elsewhere?