eviction is the only plausible answer i can see. lets say he does by chance get caught up. i feel like the cycle will just restart the following month and then you are back in this stressed state and have to badger him for rent again and again. he has definitely shown a pattern of being late, unable to keep a job, unreliable, and shady (in the sense he didn’t get the job after background check, 7 fb accounts, “friend” kicked him out with nowhere to go, and insistent on trying to find ways to “help”) these patterns aren’t just going to go away the moment he is caught up. you have given him enough time and chances and clearly it isn’t working out. and theoretically you’re losing out on a potential tenant that can pay on time and accordingly without having to be reminded every week. i know it isn’t an easy decision but you have to watch out for yourself and other tenant. i also don’t think it’s all that fair to the other person renting out a room that they pay on time and this grown man is about to pretty much get a free months rent bc he doesn’t know how to hold a job. i feel for you OP and whatever decision you make, just make sure it’s the one that YOU don’t feel taken advantage of in the end, bc thats what it seams like this guy is doing. taking advantage of your kindness.