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My questions are: What is the best approach to finding properties that will cash flow when the general rental income for a given area is low relative to the price of properties?

Even if they lower the rent to bump occupancy, the net result is the same as it relates to NOI. 

Any success with contacting the individuals skip trace shows may be relatives?

Its climate and relative isolation work against the girlfriend's health & profession though.

I’m also relatively new and this is really a foolproof affordable means to try first (cost of paper and stamps).

Wouldn't the price of points and rates be relatively equal?

The actual margins are largely going to depend on the level of finish that your client intends to complete relative to comps - no need to put luxury finish in an area where the attention to detail may not be as well-appreciated and vice versa. 

Usually less than 3 years.familiar with life settlements.. those are not life estates as it relates to a deed in real estate..  

Also each state in the US is very different in its laws with regards to landlord/tenant relations.