You will find tenants MANY times are not the most communicative or helpful sort.

Having skin in the game definitely makes borrowers more motivated to follow through.

. - The seller has no interest in keeping the property (I guess that makes her a motivated seller?)

Give us some color… days on market, estate sale , divorce etc. what's the motivation 

Investment Motivation: It’s smart that you’re thinking about tax implications.

Real estate investments can be great so hopefully you can apply what you've learned here so that if you decide to try it again you'll get a better outcome.I think what may have went wrong here is you invested in real estate at the wrong time, and with the wrong operator (syndicator), and perhaps didn't have the expertise to sort either of those two factors out.  

Your state may differ somewhat, but there is almost certainly a similar law of some sort.

A “sort of” competitor of mine who ran a small private lending fund was always operating in a fiduciary way vis a vi his investor’s capital.

I wanted to commit to learning as fast as I could and knew that if I put my money on the line, it would be a constant motivation for me to maximize my ROI. 

I know that insurance companies will do this sort of thing.If you are interested in this sort of thing, list on Furnished Finder.