It can be done well.  

These areas were economically hurt as well. 

Well I wanted to buy a home and that was the only thing I found within my price range How did you find this deal and how did you negotiate it?

With a 30-year amort and 10-year IO options - as well as ability to get rate down quite a bit if you have long-term horizon (5+ years so don't mind prepay) - the rates/terms and monthly payment will likely be very attractive.Others too have done the DSCR Portfolio Loan (Blanket Loan) refinance option too (refinanced the 10 properties that are under conventional into one blanket DSCR Loan and start the process back from 0 on conventional), however, given current rates, don't see it a lot currently since the refinance would typically mean racheting up interest on those

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. 

VA loans are owner occupied loans so not moving in within 60 days really makes it an investor loan which is not the intent of the VA loan.Now if you move in and 1 month later you get orders, well, that is fine. 

You can also have multiple VA and FHA loans as well if the situations ever arose.  

Which means a better interest rate for you   I can pair you up with realtor and I have a mortgage broker in NY for you as well.

Looks like you've gotten a lot of great feedback, but I'll throw my two cents in as well.

The FHA / HUD  listed properties , shows  (  Insured or Un-Insured  ) next to a property , as well as a Report showing the property condition , as well as any repairs that are deemed " Mandatory " to be fixed .