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.

Expect any step needs to play well w/1031.

Other factors though may come into play though.  1. 

It seemed like a long-term play with less price or industry volatility.

It's playing with plutonium.

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

A tiktok live of a dude playing a long haul truck driver simulation.

We're probably not going to take the risk if we're busy agents to play that game. 

I highly recommend working with him, but only if you're willing to put in the effort to build a business and though leadership brand!