The insurance looks as though it reflects the as-is condition.

There are probably State laws that apply as well as local ordinances in some cities.Although I'm not 100% sure, I THINK a landlord is required to keep the rental "habitable" which I think includes things like hot water and a heating system but not things like lawn care or air conditioning. 

But, a typical plate compactor isn’t going going crack a slab, I don’t know the soil/foundation conditions of your raised structure.

The IRS is specific that this rule applies if two conditions are met, it must be used for personal as a residence and rented less than 15 days. 

You don't need a property manager if the property is in good condition, you can visit occasionally and you are willing to use online recommendations and find maintenance people as needed.

Make sure you tell him, in writing, that you "appreciate his cooperation in allowing you to show the unit in a clean and rent-ready condition" to aid you in getting the unit re-rented as quickly as possible.

It was very outdated but in good condition.

The important part is probably to disclose your clients are using private financing, and that the lender is okay with the condition (of the asset) IF they are.  

Given the use, I would want to see if there are any concerns with the condition of the property.

Ultimately, depends on the size of the house and condition.