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? 

Here's my dilemma. . . 79k seems a little steep.

I am in a dilemma and need some experienced advise.

I am in a dilemma and need some experienced advise.

The book(s) are worse than j.ust out of touch with current regs, they are dangerous to the financial health of the newbie who assumes the books are current viable business models.Proceed at your own risk.  

In addition, 99% of brokers will never have seen this kind of novel approach to “solving” the owner’s no equity dilemma.

I don't want to do anything illegal or get my self in a big dilemma. 

Go talk to the town - zoning, building, and health departments.

@Anna BuffkinI understand your dilemma.

FI with a huge buffer for law suits, life changes, health issues, etc.