I have a family friend in dire straights, her husband died a few years ago and her son and her self have some mental issues, they are no longer working and she collects about 500$ in social security.

I had my mental estimates of what things would cost, mainly cost of the product and general labor costs if I used Home Depot or Lowe's, and had that as a round about idea going into the first rehab.

And I had the same mentality you did with this statement on your post "I'd like to find a property that I can fix up cosmetically to raise the value of the home & provide me with cash flow in order to start saving for my next investment." 

Yesterday i went there to clear a slow drain in their tub and i was bullied by the female tenant who accused me of putting them in a health risk due to mold in the washer.

So id say I'm mentally aware of the whole process and what's to come, but naturally I don't have actual experience until I start and that's never changing unless I do.   

The contract nature of their employment also means I won't need to provide benefits (which is fine for them as they already receive government-funded health insurance coverage).I am aware that dealing with family in this way can quickly become complicated, so part of our contract will be a periodic performance assessment to make sure they are doing a good job.

That's the beauty of the REI world: lone wolf or pack mentality, there is a lane for you. 

I like Vilas county I thought they were pretty easy with them but I knew you have to go through the health department I’m looking at a place in Boulder junction.

Deliberately have a few challenges in your screening process - it will weed out "entitlement mentality" problems4) Allow payment plans, but create system to track when payments due, so they don't keep falling further behind You will need to call them on due dates or they will fall further behind Be prepared to give a strong NO when asked if you will change rent due dates to "make it easier" for tenants to pay rent based upon their SSI or paycheck dates.

He is a great partner just has a health issue that seems to be a problem for some of the insurance companies, he is actually takes really good care of himself and is in good shape.