I have seen swat teams raid neighboring units managed by slum lords who didn't screen tenants, I have dealt with abusive boyfriends putting my tenant in the hospital, broken down cars (which leads to them missing work because they can't afford to fix the car, which then leads to them loosing their job and then getting behind on rent), being threatened with a gun (guy lifted up his shirt showing me the gun in his belt), to countless sob stories. 

(homeowner has broken roof).Where do I start with the evaluation of whether the home owner is worth lending to?

Please avoid ordering from him as he won't ship the cabinets (or send broken cabinets).. then insult you with a fake refund that goes NSF.

another thing that occurs to me is something that you should so anyway: regular inspections. quarterly, or at least semiannual inspections are a must. and make sure the tenant knows you're coming through at those intervals, because you want them on notice that you're paying attention (e.g. grow houses, broken stuff, holes in walls, etc.).

Repairing a pipe of this type requires cutting out the broken section and replacing it with CPVC.

Are you saying you sometimes pay your plumber to fix broken toilet for your tenants from same account you buy your groceries? 

Broken screens and blinds - damage. 

A dirty broken down washing machine is a big turnoff for prospective renters and even current renters might think you don't care about them.

Here's the scoop:The house has been a rental for @ 6 years with decent income; clearing @ $6k + annually; no mortgage; current market value @ $160kI have probably broken even at this point with initial cost and all (many many) upgrades;  have no idea what the tax situation will be if I sell; would not be able to use 2 year personal residence - no cap gains rule.  

Hi,We have a small SFR with some broken cast iron fittings and possible other problems.