Am I being too generous?

I have rented a room in my place to this guy since July. He has a criminal background and the best job he has ever had has been fast food. He has had issues being on time or paying rent and I have tried to help him. At times he seems ungrateful and disrespectful. He has a kid whom comes around every know and then and I have tried to show compassion. I think a big part of his financial problems are his lifestyle as he often never has any money, but he continues to smoke, eat out, do take outs, and live for his pleasures. I have tried to reason with him on saving money, but its like reasoning with a brick wall. I just wonder if I am being too generous. I mean if one is working in fast food for a career and has a kid, then it would be wise not to own a iPhone, however there are exceptions and I don't know all the details. But I imagine paying child support and all things can get tight. They do have Credit Cards which are not ideal, but better than being late on rent.

I like to help others, but people that are lazy, undisciplined, and such I have little compassion. He does not own a car, and I have tried to help him in finding a beater to drive, but he does not listen and would rather do take outs, go out to eat, and chat on his phone all the time and watch lots and lots of TV. I have offered to pick him up beans & rice, and other cheap and healthy foods to eat, but he does not listen. I am just wondering if I do not give him his 30 day notice this is going to cost me money in the future. I mean one month he did not pay at all, but claims that he did. I have a rental receipt book and keep records so its all in his mind on how he thinks he paid rent. What I have done is made an even split with the rent and utilities which may have been very foolish on my part. I mean if he does not pay and I give him his notice (the next time he does not pay rent I will) it would be difficult to bring him to small claims court as its not like he owns anything. Thanks for the ideas as maybe I am being too compassionate and gullible.