I am always a bit skeptical of home warrenties anyway as I know a lot of people that have tried to make a claim and either never were paid or were only partially reimbursed.As far as actual insurance goes, on a rental property you should be more concerned with liability and damage from events such as fire, flood, wind, hail, etc. 

Once we realized that the grass is not greener on the other side, the damage has been done, and it has set us back a decade.

When I took the bootcamp years ago, I personally found it very enlightening and learned quite a bit on the trip (especially on the bus trip where we boarded a bus and Lex physically took us to, and walked us through some bank owned houses). 

If your tenant's rent deposit ends up going on utilities and there is damage to the unit you can end up coming out of pocket. 

Sounds like in the past people were all cash buyers but didn't put up much earnest money and backed out damaging the seller.Even when you put in no contingencies many buyers are flaky.If the purchase was for say 60,000 and you put up 30,000 non-refundable money that gives the seller the warm fuzzies that no way you will back out.

Having already been through this before I know they will hit is for missing siding, the whole said of the front building needs to be re-graded, the roof needed replacement and is causing water damage.

You can charge any damage. 

If the roof is badly damaged or worn out then I would replace it with asphalt.

I have not physically been on the inside of the home.

Collect a pet deposit, but remember that a "pet deposit" termed as such can only be used for pet damage and not just any damage.