Your general business insurance may be enough to cover you for a negligent act, but not a willful act.  

You can certainly try to get the tenant to pay for the window (or part of it), but I'm telling you if they refuse there is just no way I see you being able to hold them responsible for it unless the garbage can was placed in a way that was so blatantly negligent that this was a foreseeable outcome (nothing of the sort was mentioned in your original post so I didn't assume that was the case). 

Also if you are doing something the courts deem as negligible, you are going to be personally held liable anyways.

The extra 5% is enough to allow you to buy your 5th property a few months earlier, while the added .5% in rate hike is almost negligible in the 5 year mark.

The cost of a SD 401 K loan through my provider (mysolo401k) was negligible.  

But if you have done something negligent that harms your tenants your screwed LLC, Partnership or held personally, negligence is negligence and they will get you if they have a good lawyer.I personally own some houses in an LLP and some personally, I just have very large Liability coverage and an Umbrella policy that extends to my rentals as well.Disclaimer I am not a lawyer or an accountant... just sharing conversations I have had with people claiming to be lawyers and accountants. 

Usually negligence would be covered under the contractors general liability insurance not a bond. my opinion do not hire whoever you said has a expired bond and multiple violations with state.

Seems like Every time I see these stories on here it’s a negligent pm ripping off some left coast person that bought in the Midwest for cash flow 

Though, the appreciation of this property's value is slow to negligible. 

Because of his negligence, the new "tenants" claimed they rent the house and the cops went away.