I'm probably not the ideal person to answer this question, considering I fall under your category of "habitual cheater." i just posted a discussion called "Sex addict or cheater?"
I will tell you that 10 years ago, I cheated the first time. It lasted about three weeks and I stopped. I confessed to my husband of my own accord. 6 years later, I cheated again, this time with a few different guys over the course of a year. He found out from a relative. I started going to counseling, thought I was getting better, and just three months later, did it again. Finally got back with H, then two years later cheated again. It was a 2 week A and I realized really fast, after the very first time I was intimate with the OM, that I didn't want to go back down this road again. I cut it off, came to my H and told him I was "about" to have an A and told him I was sorry. I finally (just last week) told him the real truth about what actually happened then. (that was over 9 months ago)
I am a great wife when I stay focused on the family, but when I look in another direction, I get side tracked. Am I worth keeping? Well, H seems to think so. I cook, clean, I am funny, I am a singer, actor, and dancer, good to my husband, an excellent mom, we laugh all the time, I rub his back, etc. All the things most men want in a wife.
I have a problem. I feel like I won't do it again, because this time I stopped the A of my own accord and went to hubby to stop myself from going further and I also confessed later without being caught or forced to. I see that I am getting better and making progress and I am deffinately going back to counseling, but who's to say rather I am "worth" staying with? I guess it depends on the BS and what they are willing to take and what I have to offer during the great times that might help him better deal with the hard times.
Now please don't misunderstand me here. I am not bragging; I'm quite ashamed of my behavior and when it happens, I realize how much it hurts my H and how he doesn't deserve it, but to answer your question, I had to explain that I am what you might call a habitual cheater, but I am making progress and how do you know when enough is enough? Well for everyone the answer is different, but I am more than eternally gratefull for a spouse who has compassion, patience, and forgiveness that far exceeds normal human nature.