By addressing obvious repairs now, you prevent him from exceeding the amount of his deposit at move-out and trying to skip out on damage costs beyond his deposit.

Usually after 12 to 18 months of vacancy the city will convert the zoning to conforming from grandfathered, which will prevent the usage as an MHP.  

Do you use any tricks to prevent psyching yourself out?

I agree a nest egg is essential to prevent a personal "financial collapse" but when you have a 3.5% interest owner occupied loans over the last year or two, after tax deductible interest is really like 2.5%, I can't see any sense in paying that thing off quickly.I do agree with the nest egg philosophy though, don't finance to the hilt and hope things don't drop out.

Always do your due diligence...when you find a county to purchase a property in, you will usually go through the court of clerks which is where you can uncover how much the liens are on the property, and any special nuances which might prevent you from purchasing it. 

Shouldn't realtors be governed a bit better to prevent this type of conduct??!  

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.