The biggest obstacle for most is the debt to income ratio, especially since Hawaii lenders are pretty strict.

Plan to build a team that you trust in the area that can routinely check on your property in the event you don't live nearby to perform regular quality checks.

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

In order to protect economic stability in such a hot vacation location there is extensive and strictly enforced leasing restrictions on the majority of SFRs and condos so AirBnB is not an option for many owners. 

In all my years the operating costs of a property have NEVER decreased & much higher property taxes are inevitable so unless you're in it to lose money, or bought into strict rent controlled housing, rents will have to rise. 

This is why we state our criteria to depend on credit history (which of course includes score) rather than strictly score.

I’m looking into buying my first home before I get out the military, I strictly want the property for cash flow wanna be a landlord

I learned that the VA is strict when it comes appraisals and will not lend more than what they value the property at.

We routinely find deals between $200-$300/door, mostly 2-4 unit MF. 

I have no strict/pressing timeline to move, so if that is probably the best way to meet my goals and still within my budget, I am very open to it.