For the most part I don't think it is that hard and not as hard as most people think.#2. 

At least I think so.

By conservative -  think less than 65% LTV, high Fico, and DSCR over 1.0x.

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. 

Or are there any other "creative" strategies somebody can think of for this? 

I was thinking maybe we could set up a ACH auto withdrawal from her bank or unemployment card to ensure the rent, any thoughts or complications with that? 

If the attorney thinks it can be done, obtain a title commitment before starting so you can be reasonably sure a policy will be issued when you're done.I have run into situations where some of the heirs of the property owner have themselves died leaving heirs and beneficiaries and sometimes some of those heirs have also died. 

I think you should maximize the guests and maybe offer a small weight set and yoga mat. 

Most professionals will recommend a separate LLC for every $1 million in assets but I don't think that's necessary.

As  you're probably already thinking as your reading, I made a huge mistake.