We live in Kihei now since the Lahaina fire destroyed our home, office and an investment condo.

For reference, we're heavily involved in the co-living space, which is an unorthodox strategy but can perform exceptionally well with the right property and systems in place.

I used to live in Tokyo for 6 years and would like to find a reason to go back more regularly but let me know if you want to connect!

The loan is with you, not with your tenant, so none of that means anything to them - in fact because you live in one unit and it's under 4, if you were self-managing you don't even have to abide by fair housing laws (at least on the federal level). 

Businesses are “living” organisms with a life of their own, usually having deep meaning to their owners.  

If they do, you may have a chance under the scenario you're proposing - if they share your concern for it's condition (although that seems unlikely since they've been living with it the way it is for some time, it seems).If you own it, it's pretty lowbrow to expect a neighbor to invest in your property. 

Sure for most occupant home owners with no money in the stock market and cash tight perhaps (just my views mind you) use of their HELOC to have a house they live in paid off sooner makes perfect sense. 

I used to have a two bedroom apartment that I lived in and I would rent out the second room on Airbnb and one time I got a guest and she would leave her windows open.

I too live in Asheville, so Sapphire was closer than Cashiers and Highlands.

I realize people are trying to make a living, but anyone who cold calls me is the last person I'd use for any transaction (plus I have people for that!).