You want to play the charitable hero.

Umbrella insurance will never come into play for Property damage (fires, storms, floods, etc.)It is liability coverage only.I'm an insurance agent and have seen umbrella claims from fatal car and boat accidents. 

He’d likely play the role of buyer’s agent, contractor, and rental listing agent—something we successfully did last June.

Not the cash flow play a lot of people expect. 

Sometimes the best investment is found in a 'transitioning' market that is just outside the 'great' market and is in play to be the next great one. 

How will it all play out? 

Better play it safe and use a warranty deed instead.Also, later on when you sell your property, it will keep the chain of title cleaner for the next title insurance.Last but not least, a warranty deed does not cost more than a quit claim deed...

Curious how this will play out in the courts (granted it's LTR) and affect pricing products used for STR such as PriceLabs (which I use but have to seriously manually adjust for very specific reasons).

This specific tenant disregards quiet hours and continues to play their music loud.

On most any day you could find people walking dogs, or children playing in the area.