You're right, it's become more and more a charity service to keep this guy in his home, which adds additional problems in itself.   

I'm simply a means to an end for them, I'm not a charity and no one should expect that of me.

What you are talking about is a charity.

Which happens to be province with laws that are absolutely terrible when it comes to landlording.For example:You cannot collect a security depositYou cannot ask for first and last months rent (although people do, i'm sure)Tenants can pay consistently late by up to 3 weeks and if you cannot prove to the court that their consistent lateness has not cause you financial harm, well too bad for you.You can't charge late feesEviction is almost impossible - even if they completely go against the lease i.e pets, airbnb the property when you forbid it, consistent late payments etc.The province really treats landlord like they are a charity and that people landlord out of the goodness of their hearts, when reality it is a business.So here is my question,Is it a good idea to invest in your first property out of the Country?

There was a case I heard of where a tenant was paying rent using a check book from a charity they worked at.

However, they had to do it through a charity because Maryland law only allows charities to raffle off a house.

Cashiers checks, money orders, or ACH are the only payments I'll accept for security deposit and first month's rent.

You let someone stay in your rental for free - or at a steep discount - and they may still abuse the property and cost you thousands more.If you want to donate to a charity, rent the property to a good Tenant and mail a check from the rent proceeds.

You are running a business, not a charity...no feelings involved.

I would ask them to pay rent using a credit card and deal with paying the money later.Otherwise, you can either choose to run a business or a charity.