Just had a slew of items recently charged to me, example broken lamps, dining chair damage, blinds that broke etc that the property management charged me and not the guest.

Granted, there was a hurricane, but even without that I've had several busted screens this year from guests pushing a chair through it or some rugrat running up against it, where you didn't have any way of proving anyone specifically damaged it so the cost is on you. 

Buy new mattresses and new couches/chairs (heard bed bug nightmares). 

I have a tenant who has 2 chairs and a small table on the grass in the back yard causing my mower guy to have to stop and move it before mowing.

We bought recliners, table and chairs, offer high-speed wifi, and carpeted a play area for kids.

Sit in every single chair and see if there is a wobble and if it needs to be tightened up, check the exterior of the cabin, are there signs of carpenter bees, check my windows, any leaks, etc. - you get the idea

I met an agent this side of Knoxville, and she said,She was selling homes in Gatlinburg,I climbed up in my chair all warm, nice and cozy,Thought I'd soon be hearing from her...But tears filled my eyes when I found out she was gone, Smoky Mountain rain, I keep on call'n, keep on call'n, her nameSmoky Mountain rain, it keeps fall'n, I keep on call'n.But she's somewhere in the Smoky Mountain rain."

My first STR was a disaster- I had people throwing 20+ people parties in the small 1B1B  apartment, someone had  female issues on my light blue kitchen chair and the cops were called multiple times. but I LOVED it, made money and would do it all over.

In fact, the one dirtbag was actually sitting in the yard in a chair under a tree smoking a cigarette and listening to music as if he had not one care in the world.

It's not a continuous loop,  but you don't WANT that,  as a pet or child or chair caught just so can unravel it.