@Jay Hinrichs, Wait... are you telling me that Silicon Valley is NOT the center of the universe?!?

I would call that middle class at least, and that's assuming 0% interest on that initial $3.5M.So, you're ***-u-me-ing perfect health, no injuries / accidents, no natural catastrophes (hurricanes / cyclones, wild fires, volcanic eruptions, ... at least two of which are common in HI), vehicles which last forever and never need to be replaced, destruction-proof housing and furnishings, ...... and if you CAN live that lifestyle in HI on $100K / yr (most people can't in ANY state), why are you not teaching personal finance at the university level? 

If you are relying on this income to support the tenant's ability to pay rent and for some reason the tenant decides not to pay rent, you will have no recourse.

I understand the concern about a bubble but from what I've read the population dynamics alone don't seem to support the idea of a bubble here, but who knows.

Even though I had "Chip and JoAnna" dreams, I have to realize that I have my "job" and he has his.My properties are out of state so there really isn't anything for him to do, (but listen on yet another phone call with my contractor, LOL) but be supportive at this point.

I am Oxford University educated and have a cursory understanding of marketing through my husband who is an entrepreneur).Thanks so much for your input in advance!

They're more than supportive and will offer help any way they can. 

There's nothing wrong with risk if you have the cash reserves to support a few losses, but when you're just starting out, I'd strongly recommend finding a property with less risk.  

But I have trouble believing the numbers support it any longer.

@Jo-Ann Lapin Thanks for the support!