My $.02....For someone who hasn't been willing to follow many of the limits and requests you've agreed on in the past do you really think he's going to be willing to follow these requests???? And.....even if he says he will, do you feel you can trust him to do what he says he'll do?? If he doesn't, what will be the "consequences", if any? (I'm not saying you need to share the consequences with him ahead of time, but do YOU know what you intend to do or not do if he doesn't meet your demands?)
I've found that it's most often helpful to say what I will and/or won't do and not tell someone else what they "should" or need to do, e.g. "You really need to work on getting through this response of guilt." Instead...."I'm no longer willing to console you when you are struggling with guilt over some of the choices you've made."
I wish you well....not an easy situation!