Or if strong winds are an issue, have a structure built to prevent garbage can from blowing over.

They do a decent job of working out if you don't wan to compared to other servicers, though no one will do as good a job as you.While I can't site a specific law that covers calling them as potential not buyers, its what I was told, and if anyone knows any specific law or statues under banking laws that prevent you from calling the mortgage holder before you buy their mortgage, please do enlighten us. 

Any suggestions to prevent roof failure or leaks?

This will cut down on the tenant saying they left the check somewhere, and also prevent you from having to go pick it up.

The best lease option investor still can't prevent any of the scenarios above.

I found the owner and basically he has social problems which has prevented him from renting the property.

Also, don't let the lack of a real estate license prevent you from starting your real estate investing journey.

Prevent any potential issues. 

it won't help you with this situation, but it may prevent future pain...SOW (Scope of Work) itemizing precisely what work is to be done, the finishes and/or exact material to be used, who has authority to decide on any undeclared materials or finishes (you or contractor).

That being said, as a first time Note buyer, I am positive on what "hair" I need to be on alert for.Have not yet run a title report...and as I mentioned in my original post, 3 years of delinquent taxes were paid in mid-2015 to prevent the property from going to tax sale.