Is the extra few bux a year worth it? 

Or would be worth pursuing a R-62 Minor Home Improvement License as an extra precaution?

Not that these things keep the house from passing for a VA Loan, but that you don't have $5,000 in cash to do the Upgrades .....

Might be worth a call with a few local mortgage brokers.

If you buy a property with the intention to rehab and refinance (BRRRR) to pull your cash out, you'll need to wait 12 months to use the appraised value with a conventional loan.

The passive loss limitations for non RE professionals make cost seg not worth it in my opinion. 

I don't track the STR market closely on Big Island, but I have had clients look on that island and think you should find something there that cash flows pretty well. 

My hope is to begin the investing journey with using as much as our own cash as possible.

More on DSCR loans: DSCR loans won't use your income to underwrite the loan.DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.

You will likely be negative cash flow unless you can increase revenue somehow.