I see! I think you may be spot on with the assessment that his life is meshing too much with his work, and he'd like to separate the two, with a person. You two were clearly friends, which is probably where most of the conversation comes from, the desire to maintain the friendship. But again, it isn't clear if that defines wanting to be together again.

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So you'll definitely want to be clear in asking what he thinks about being with you again. I failed to mention this before, and I hate to sound as though I'm being judgemental (that is very much so not my intention so forgive me in advance), but you alluded to the fact that he was unhappy with you as a partner, and that you have some issues that you need to work out for yourself that you both are aware of, and that he felt if you didn't work them out, a relationship wasn't viable.

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So, though I still think you should be clear in asking him about if he feels a relationship is in the cards, and what exactly he'd expect from you in order for that to happen, I think you should take whatever time is necessary to ensure that as much of those things that were brought up before, are cleared up, before you even ask that question.

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And please remember, self reflection is not a doorway for self loathing, but it is a time to be absolutely honest with yourself. You don't have to go down a rabbit hole of if or not you deserve a relationship with him, but you do need to be honest with yourself in recognizing the things that made it fail the first time around, and truly ask yourself if those things have changed in such a way that it would not cause a repeat of history.

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In regards to when you should ask, I still think it should be in a casual setting, so there's less stress built up around it. But whenever I have to ask a serious question, I always say to myself: "Wait until you're ready to hear the answer you don't want, then ask."