House Hacking Problem: Roommate always late in rent

[Lisa Marie]

Hi BP - looking for some advice because I am in a sensitive situation. 

Basically, I violated the age old rule of rooming with friends. I put goodwill and faith that everything will work out and be OK... not. Long story short, a friend of mine is renting a room. It's been fine in terms of the day-to-day living situation and there are no issues there. I really enjoy the benefits of house hacking. However, there are a few things that have been bothering me: 

1) he never pays in full and has to break up his payments, 

2) I don't know when he's going to pay and 

3) sometimes he'll shut down and not respond / make up an excuse when I nudge him. 

Granted, he DOES pay in full by the end of the month every single time but I'm over it. Some months are great, other months he's inconsistent. I've already had at two or three conversations with him about being more communicative and to let me know when he will pay. He has financial hardships, but I've done my duty as a friend on being lenient and understanding. What really got me upset this month is when I noticed that he went Christmas shopping for gifts but has yet to pay me rent. I feel like if he were renting an apartment elsewhere, he'd get slapped with late fees over and over again. 

My brother is a lawyer, and he told me that I need to evict him because he's taking advantage of me. I texted my roommate saying that we need to talk tomorrow and he agreed. I also asked him about rent and he made up some stupid excuse... so now I'm really upset. At first I was going to say that if he MUST pay by the 1st, otherwise this situation can't continue. But my brother is adamant that I terminate this living situation. What do you guys think? How would you have this conversation? Please note that he is a friend, and we share interests and know the same group of people. :(

Thanks!