I have a tendency to be overly analytical and get stuck in "analysis paralysis" but my wife a woman of action so we make a good team.  

The woman that I spoke to didn't spark much confidence in me, although she was most likely an office assistant.

This whole insurance thing...I dunno...if a grown man/woman from CL or elsewhere takes a job and due to his own negligence (maybe on drugs, maybe not, who knows) gets hurts on my driveway, roof, or whatever, then wants to sue me because he doesn't have insurance, that just doesn't seem right that the owner would be liable.

The issue is the woman with interest in the property is MIA. 

I am renting a single family house to a woman and her dog.

There are also landlords in other areas who historically would refuse voucher folks because they felt they could not control who was living in their properties... on the other hand, years ago I knew a landlord whose very perfect tenants were a retired couple (man was disabled, woman was still able to work part-time at 68) and they were on a section 8 voucher program; the landlord wished all of his tenants were like them as rent was always on time, etc. 

The week I moved in the mother of the woman I bought it from knocked on my door and asked me if I would be interested in buying the place downstairs as well.

Current SituationI have an elderly woman who is motivated to sell her property that she inherited from her father who recently passed.

Does anyone have any experience with being a one-man/woman army in this investing game? 

A woman and her two children live upstairs and pay $1,100/mo.