I don't think it was mentioned specifically that Juste met Simon. I think it could have been either way; someone else could have given him the bracelet and..well, everyone knows the story of Simon, since he's the most well known Belmont. Anyone could have told him that story.
He could have had a wife and a baby by the time SQ happened. It would make the most sense: there was a seven year gap between CV and SQ. Gotta secure that Belmont bloodline as quickly as possibly, after all.
I think the curse's nature is essential; the way I understand it was diferent from DC/CoD; it was targeted at Simon instead of the whole land. Dracula's body parts enabled his minions being around, but it wasn't like in CoD, where people were driven to evil to "obliterate themselves". So, if Simon did lift the curse, like Juste said, it has to mean he survived. Otherwise he would have failed in lifting the curse, which would have meant it killed him.
Of course you could interpret "succumbing to his wounds" as wounds from physical battles against Dracula & Co.