When is it time to say goodbye?

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One of my best friends is attached to her boyfriend at the hip. They get in fights all the time, don't talk for several days in a row, and then make up and spend days upon days with each other. This friend of mine is the type to ignore all else when she has a boyfriend (super annoying, but I'll save that for another discussion). He's made A LOT of mistakes and they keep coming, or so it seems. He's addicted to heroin and painkillers, and has not made any effort to get help. He was recently involved in an armed robbery - as the 'getaway' driver. He lies to her until he can't any more, lies to everyone in order to get his fix. Disappears for days at a time with no word. Acts shady... I know my friend is 'in love', but isn't there a line to be drawn somewhere? Maybe because I've never really been head over heels for someone, in that puppy-love/spend-every-waking-moment-with-them kind of love, but I feel like I could not be with someone like this. Not until they changed their life, their ways for the better. I'm not passing judgement on my friend - she is capable of taking care of herself, making good decisions, etc, but I just don't understand the decision she makes every day to accept his apologies, to stick with him. I know he must have some psychological issues, but there's always a way out - a choice to be made. I just wish I understood why she takes so much pain and heartache from this guy. Have you ever been in a situation like this with a boyfriend, husband, sig. other? I must be missing something...