They may agree to whatever you propose, but then melt down when confronted with reality.

Instead of being confrontational, use this opportunity to show the tenant they valued.

These things will annoy you and eventually will put you in difficult situations whenever you confront them.3.

They said they would pay the next day, and I didn't end up getting it until three weeks later, the 23rd of that month after literally staying outside of the place and confronting the tenant who had not been responding to texts.2. 

I let them confront the fact that their house needs work on their own terms, I let them work pricing themselves while I guide them on what I've paid in other scenarios. 

In this case I would hire an attorney for the eviction proceedings .The fact that it is family  can very well put the focus of anger ,blame etc on yourself  The attorney will insulate you from direct confrontation .Reporting illegal activity can backfire and hurt your grandmother .

So if you are uncomfortable with confrontation or, ethnic customs or you just prefer to rent to people your own age, you may choose your tenant on any criteria you like. 

What do you think they'll do if they lose their job or get into a confrontation with the Landlord or neighbors? 

However, now when I want to do do the same setup I'm confronted with resistance.

I would confront the tenant and have an honest conversation to determine how to move forward.