Aloha Justin! My wife and I got stationed on Oahu in April of 2019 so I could provide some insight into the mind of a RE investor who is in the military and stationed on Oahu. My goal when we arrived was also to buy. I offered on types of properties and in certain areas of the island before I was educated and knew the island. My first bit of advice would be to get here and use your TLA (temporary living allowance) while getting a feel for the island before making offers. 30 minutes of driving on this island will take you through 5 completely different towns with different feels, traffic, home evaluations, etc. Just because the island looks small on a map doesn't mean that every town here is the same, not even close. Know the island and where you and your wife are comfortable before you offer and get stuck somewhere. After unsuccessfully offering on properties the first go around, we've been renting for about 10 months now, and I am deep into the home search once again. I offered on a property last week and we're in the thick of negotiations. Complete house hacks may not always be possible, but heavy mortgage supplementation is definitely possible and worth shooting for, as tons of homes here have mother-in-law units (or Ohana units) on the property for great rental income. So, although you may not be able to cover all $3K of your mortgage, maybe your 1 bed/1 bath is bringing in $1200 and bringing your mortgage down to $1800K, super helpful! In addition, don't let the hefty prices intimidate you as we have a great advantage with 0% down, or close to 0% down, VA loans. Great opportunity for "free" appreciation!
All in all, do what's right for you and your wife, but choosing Oahu has put me out of my comfort zone in the best way and made me experience adventures, friendships, and culture I never would have on the mainland. Has it delayed my investing career? Unfortunately yes, but I know in 10 years when I have 15 properties I'm going to be talking about and thankful for my time here. It's also help me become more educated and savvy in OOS investing. Hope that helps - feel free to reach out if you have any questions I'd be happy to help!
Shoots -