Follow through with the notices to pay, do not simply allow her to pay late without giving her formal notice.

Of course real estate investor would be the easiest out of the choices because there is no formal education or licensing requirements and there are numerous ways to invest in real estate.

So long as you don't formally represent someone or informally suggest that you're looking out for their interests, such that they may think you're representing them, you'll avoid the vast majority of conflict issues.

@Kim Meredith Hampton I hadn't heard of roommate lease form, but that certainly seems more formal/binding than telling them to simply deal with it.  

Make the letters very short w/o any threats or formalities e.g.

I have a great deal with a super motivated seller but he has self managed since he purchased the property so he has no formal records but in my assessment his properties are a steal.My dilemma is all of my investors like paper trails and are to nervous to take the risk how can I make to deal work without the normal paper trail.

In addition to the above, each LLC will need to have it's own books and records and follow formalities.

I have a pretty good gameplay but I would like to hear form all of you as to what your course of action would be.Thanks,Chance 

Will counties generally negotiate in a case like this so they get something or will they generally stick to the formal (slow) tax lien route? 

They are on a month to month agreement, and to terminate you might be required to give them formal 30 days notice to terminate the rental agreement.