It might be that he is thinking (or unconsciously allowing himself to assume) that I will convert...However, he tends to minimize the differences that remain, and I find it quite difficult, sometimes, to know whether or not his view is likely to be shared by the Church as a whole (or by his priest). I think he's liable to go into things happily assuming that the priest will say, 'oh, yes, fine', and it seems to me this is a slightly dangerous attitude.
You have identified some very important points and I think you are very wise to have a thorough discussion beforehand so that you can identify potential "landmines." Much of this conversation, though, IMHO, should be taking place between the two of you and his priest, as a part of premarital counseling.
Also, when you mentioned that his parents have an idea that he should be a priest, that could be another potential problem. In order to be ordained, an Orthodox priest must have a wife who is Orthodox also. If he doesn't feel that he is called to the priesthood, it might be a good idea for him to tell his parents that. To avoid you getting blamed for his not becoming a priest, you see.