you're rationalizing why you fucked up and weren't honest.. Nothing above is about how you fucked up. Its about his fuck ups. Which to me is completely separate and totally irrelevant. Whatever your preference is don't tally up someone elses problems to make yours seem less important. Just fucking tell him you don't want himand tell him why. The only toxic part is someone lying to someone else about what they think or feel because they are too scared to relay the truth . I find it especially toxic that you will probably continue to be his friend while you harbor all your feelings about the way he lives. You are basically the problem. His self deprecation is a flaw that can be fixed. Yours can be too if you just own it.