Some areas and lots use well water others have city water.

Are you planning to invest only in your local market, or are you open to exploring opportunities elsewhere as well?

She's a realtor as well and we find that no one cares about your properties as much as you, so over the years we've become GC/property manager/realtor. 

I would expect the success rate to be well under 10% and the make back your money claim to be a best 25%.  

It can be done 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.