@Cameron Riley
This may sound self-serving, and perhaps it is, but I have some experience and this is what I think I've learned.
Every society has limits. When members of that society exceeds those limits and harms that society, they come up against some of the institutions that work to bring them back to within those limits or expel them completely.
I don't agree with all the precepts and treatments of the Alcoholics Anonymous program, but there is a psychological concept of "rock bottom" in the program that I do think has a lot of value. According to this theory, addicts can't really commit to getting better until they touch rock bottom in their lives, realize the harm they're doing to themselves and others, and consciously decide that that going on as they have in the past is not an option.
Also in addiction treatment, there is a concept of "enabling." An enabler is a figure in a troubled person's life who enables the addict to continue on in their troubled ways well past the point that they should have seen the error of their ways, shielding them from the full impact and consequences of their behavior. The enabler does this for a variety of reasons, many of them well-meaning.
For me, every eviction I have been involved in has been more than anything else a process of stepping away from enabling and clearing the way to rock bottom for a tenant who needs to seek help or treatment but refuses to do so because they're terrified, they're proud, or they're blind to the consequences of their ways.
You have to decide, as a landlord, if you're dealing with a person who will seize on an opportunity to change their behavior if you give it to them, or whether you're dealing with a person who will not change until they hit rock bottom. If you decide on the latter, you're not doing them any favors standing in their way, and enabling them is ultimately harming them.
An eviction triggers a whole host of social services and safety mechanisms that are there to help the troubled tenant. That notice on the door may be the only way the tenant will ever actually first reach out for help from the people who are there to help them.
Now let's look at this case and what you've told us. Your tenant is 20 days late on the rent and he doesn't have the money to pay. He has been there for a year. How did he end up in this situation? It didn't happen yesterday. It took a series of bad breaks to get where he is, I'm sure, but it also took some bad decisions on his part, and he is responsible for those. If you DON'T evict here, you're offering one of two things -- an opportunity for this person to radically change their behavior or an opportunity to keep on as they have been keeping on.
Which opportunity do you think you're offering? If it's not the first, then you evict. Because ultimately, it's the kindest thing you can do. You evict because that's the only message that will really get through the psychological blinders this guy has been living with. Do it decisively, do it according to the law, give this person every opportunity to get the help he needs to change his life.
I don't feel guilty today about the evictions I have initiated and seen through. I did not make the decision to evict in anger or out of spite, or based on what would financially benefit me the most. I stepped away from enabling an adult not to hit the rock bottom they needed to hit in order to make their decision to change.