You could arrange for the sale through a local realtor as a way of helping her.I think the biggest risk is owner financing to an owner occupant who depletes the property's value by not maintaining the capital expenditures (roof, systems etc).

I do have a full time job as a Systems Safety Engineer. 

The city provided a honor system of paying taxes on these rentable units and out of the thousands of homes that were given notice only one home/owner landlord complied.

We do not use the letter system for acquisitions at least here in the Chicago Market.

Our long term goals are to build a system and team that buys and holds single family, multi-family, and commercial properties for cash flow.

Have you tried his system?

There will also have to be seasonal maintenance activities such as cleaning of the gutters, emptying water out of the sprinkler systems, etc. to eliminate some of the weather related issues. 

I always charge for shampooing because I have a professional system and I always do it on turnover.

If he were to flake, he's got all the wrath and power of the legal system on his side.

You wouldn't believe how landlord unfriendly the legal system can be here.