Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

So, for items #1 and #3, I would talk to them directly first because I like to treat people like people and communicate directly about anything.

how do people scale their subject to deals

If one of those people doesn't pay or they move out, you're taking a hefty hit on your cash flow for sure. 

A festival that draws 250k people is pretty big time - are you sure about your numbers? 

Looking for advice from people who have been in the rental business for a while.

Those are the people you want to talk with about this.

It’s not worth chasing people around for a buck in my opinion.

It seems often that people will dwell on books, articles, podcasts and other sources and really just need a bit of personal motivation by peers to get out there and take that risk to start gaining those Street Smarts. 

Are people clicking on your listing and not booking?