No tenant, no matter how good could leave the place without some disrepair in 6 years.Tl;dr 40k house on market 200 days, wondering why an investor hasn't picked it up if the simple act of getting it is already positive cash flow. 

You picked them because they were qualified.

AKA the actual rate of return on a property you are feeding will generally be poor and you would be better off with a better cash flowing rental or in the stock market.Of course, if you found a great appreciating market or structured the debt to be shorter term, feeding a rental could work out well.

I know you said you didn't want to get into the long story behind quitting your job, but from the info you provided it sounds like you should probably pick a lane and move in one direction for a while.

I'm ready to pick up some turnkey vacation rentals on the island as people stop doing it!!

No, the landlord picks up the vacant space. 

Here are some of my favorites that helped me to get started:Rich Dad Poor Dad - Robert KiyosakiLong Distance Real Estate Investing - David GreeneThe Book on Investing in RE with No (and Low!)

The reality is that opendoor, zillow, etc are making some pretty poor purchase decisions, that a seasoned trustee sale investor wouldn't.

., you have relatives who live there), then since you're going to do Long Distance investing, my thought would be, why not pick a place where there's some kind of trend happening in favor of that area.

Basically Anywhere that offers poor cash flow is going to be a hot market