Of course, every owner's situation is unique and factors like the legal entity involved, purchase date, adequate passive income that can be offset with the cost segregation study, etc., will need to be considered.

Alternative is the sherif evicts him and I pay tax and insurance.I know we can have a gentleman's agreement on these things, but im still afraid he might be able to legally sue me if we have a legitimate residential lease?

You may run into issues with re-tenanting and it may take longer than you expect or cost more.  

The taxes are higher, the properties are older, however we account for those issues.

Should I be concerned the bank may have issues with this? 

And agents are legally prohibited to engage after closing - at least per Wisconsin State law. 

The worst part is they refuse to help me get the account back, quoting their terms of service and stating they are not liable for any issues with my account. 

And never being “at risk” is it even sufficient to legally bind a seller?  

Or this is a non issue if insurance coverage is not taxable.Many other thoughts and input.

Double check your lease, all the legalities and still check with the landlord....