With regard to my parents, I want a good relationship with them so they can build my credit history.

You don't need a PM if your parents live there.

The month of June my parents stayed in the property from out of state (the whole reason we bought it)  July was $2200 (only 3 weeks mom and were here first week of July).  

If I had a kid like you in my community, I would be happy to let him/her help me with tasks in exchange for training.Do your parents have good credit?

My parents have a fully paid off property they have turned into investment for quite some time.

I feel at this point trapped by the Analysis Paralysis syndrome, as well as time and energy starvation due to a full time job and role as a single parent.  

We require any tenant 18 or older to qualify for whole rent on their own unless they are a legal dependent (spouse, college student, dependent parent, etc) of applicant, even then must pass criminal background check.

I do have a possible opportunity to buy a home that was left to a friend if mine & its full of stuff left befind if his parents.

After three weekends' of showing to about 15-20 groups of people, I decided to rent to a couple relocating back to California (credit it 580, lower than my required 650, but with parents as co-signer, parents have good jobs and own a house, and local in town).

Their parents need to approve the purchase.