Obviously there comes a time to do a full replacement (you don't want to risk a major leak/damage to the interior), but if you can spend $500 now and get another 5 years out of the roof as is, that might be a good business decision. 

With the damages on your property, coupled with the insurance problems, I will suggest (1) sell it AS IT IS. (2) If you think and/or you have that $32K to fix up the new damage, fix it and put it back in the market for REN-TO-OWN, this time around you will NOT need a property manager.

The only way to remove this from the wall is to use a diamond blade grinder and cut into this and score horizontal, vertical and diagonal lines and slowly carefully pry or chisel it out piece by piece trying not to damage the adjacent tiles. 

You might not get pending divorce cases handed to you but you can likely find probate, code violations and possible damaged homes pretty easily.

It won't be any skin off his nose at the moment, cause he isn't getting paid right now anyway.  

And the other thing it does is that, if you were to get water, the floor wouldn't be damaged nor would you have to deal with a tenant calling you telling you to come dry out the carpet before it gets mold.

But I would also want at least a 10% down payment, since if they stop paying and you have to foreclose, you could easily spend more than that in lost rent and legal fees, plus any damages to the house.

Bad neighborhoods will cause a long time period to rent out to better class of people.

You are going to have to do some damage control.

Either the houses are too damaged and not worth the repair, or they are priced too high for a return profit.