Not many companies off comprehensive STR insurance but there's a few, and you may get extra coverage on loss of rental income, bedbugs, etc.

But that is just with our occupancy rate, posted rules and extra fine for breaking said rules (spilling drinks, food, dirt, etc.).But only you will know how often it needs to be done.

Consider it a loss and tell them they have to move or you will start the eviction process.

The job loss was news to me...

My rule number one is- don't have losses. 

What’s your “loss”?

For educational purposes and future planning, is there a downside to having a large net operating loss carrying over into future years?

I feel that the potential is their if its in food retail or solid tenants not offices.

You aren't going to take someone to small claims court for damaged paint or anything, and if a major loss occurs the tenants are almost never collectable anyways. 

You have to have someone fill in the gaps for you.You can do this on your own, don't get me wrong, but the time loss and the costly mistakes don't make that approach worth it, in my experience.