I still owe around $8K in student loans that I've been paying just over the minimum monthly on auto-pay since 2012. 

If your tenant loses their job, gets transferred, divorced etc during the term of the contract I do not feel the PM company can foresee that any better then saying you will not be in a car accident this next year...

Don't like how rent is received 7+ days into the month but great from auto billing late fees and avoiding those harder conversations. 3.

I haven't used Liberty Mutual for landlord insurance, just my own home and auto.   

If you add them and they cause and accident or need to go to assisted living the lawyers or the government will want the house. 

Another carrier that can do stand-alone umbrella policies (meaning they do not have to write the home or auto coverage) is RLI Insurance.  

My payment for the primary residence are auto drafted.

Credit card debit and auto delinquencies are off the charts!

He requoted all of my policies including auto and umbrella. 

Its your responsibility as a landlord to provide a safe environment to your tenants.Regarding the insurance, I would definitely seek to have the property insured for peace of mind and to cover yourself from a legal perspective in case there are any accidents that happen on your property.