You're analyzing it way too much, Plumeria. (That's what we NT women do - we talk to our girlfriends for hours wondering "why this" and "why that" about certain things that are bothering us until the subject is just talked into the ground and we still don't have any answers.
) Just contact him, make conversation light and let the chips fall where they may. Otherwise, the not knowing is going to drive you crazy - it would me.
Another thing women do (I don't know if men do this, I just happen to have seen it more often with women) is set up a test to see if the guy really cares about them. The thing is, the test never actually proves anything, except in the woman's mind. Because there can be different reasons for someone taking an action, or not taking an action. So someone thinks "If he does this, or doesn't do this, it means he cares about me, or doesn't care about me."
I think the test you are setting up, is him contacting you first. A really common test women set up, is to wait to see if a guy takes initiative, and if he always makes the first moves. Well the thing is, there are plenty of creepy guys out there, who, while seeing women only as sex objects, who are willing to take the first move, and willing to pursue.In fact, no guy is better at pursuing than some crazy ex, or some crazy potential rapist/stalker. Pardon these extreme examples. My point simply is, that someone taking the initiative, or not taking it, pursuing or not pursuing, is not a true indication of whether or not someone actually cares about you.
If you reach out to him, and open up the possibility of getting back into a relationship with him, he will not get back into a relationship with you if he doesn't want to. This is both good news and scary news. Good, because in the event that you do end up together, he will do so because he really does want together . Scary, because of potential pain for you if you end up not together after all. Sometimes fear of the possibility of that pain is the real reason why one chooses not to contact someone.
The most important thing to remember, is that every relationship has difficult parts, and times when there are problems. And what exactly those difficulties and problems are varies, from relationship to relationship. The question is are the good times more frequent than the bad? Or do the lousy times outnumber the good times? Does the good outweigh the bad, or vice versa?
(It should be mentioned, that there are situations where a particular bad thing is so wrong, that one should leave, regardless of how great the good parts are, for instance, when there is physical abuse.)
From the way you have written about this, it sounds like the good outweighed the bad, and like it could once again. But of course, the decisions are up to you.
Regardless of whether this ends or continues between you and him, he was very lucky to have met someone as understanding as you seem to be. I think he will remember you with fondness in any event. (he reminds me of my best friend, who does definitely remember past persons in his life).