You don't have to be cruel about it but you do need to decide if you're running a business or a charity that subsidizes living expenses of strangers.

Did you buy this property as an investment, or are you starting a charity?

Have a charity list available ready to send to tenants who are behind. 

You are running a business, not a charity. 

This is a business not a charity.

You have to set boundaries from day one with tenants, be a LITTLE flexible when "life happens", but run your business like a business, not a charity.

Knowing the process for this county is key as some places force you to work through a charity or fund to help tenants get caught up.I would 100% talk to the seller or the sellers agent and get as much info as you can on where things are at and proof they are at that stage. 

@Matthew Chalfant This is a common question on the forums.....the answer is: do you want to run a business or a charity?

However, I do have a very basic goal of setting aside money for investments, constantly looking for deals, continuing my education, and improving my portfolio.This year I bought an investment that is also a charity.

Like we say on here all the time - 'Are you running  business or a charity' ?