Furthermore, the behavior is causing me mental, physical, and financial stress.

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.

That is a mental block I need to get past, my inclination is to demo the whole house and build a pristine new home, but of course that is a lot lower return than rehabbing a property to the point of just "good enough" and moving on.

Huge (sometimes exhausting) learning experience for sure!

He's definitely going through some mental issue's and I feel bad for him but I need to take immediate action.He's now gone for 2 weeks, his unit is oddly cleaned up with furniture strategically placed to cover up certain holes in the walls.

Plus, they help with the hassle factor of coordinating everything and the mental load.

I don’t fully subscribe to everything he says, but he’s not wrong when it comes to the mentality behind what I’m saying.

The right to remediate is important when you have tenants with challenges (physical, mental or emotional) that interfere with their ability to maintain a clean unit

Buy and Hold mentality, while collecting returns.  

Would a new exhaust system, for example, be depreciated rather than expensed in that tax year?