In Reply To #1
Well, I would like to say I'd put Legacy of Darkness and Castlevania 64 back in the canon, but I don't even know why they were removed in the first place.
Anyway, I'd make that missing 1999 game, making Julius and his group go to Dracula's castle, and battle Dracula. They make it to the throne room, where they battle Dracula's servant. When he is killed, Dracula then retreats into an alternate dimension to save his own life. By journeying into this world of darkness and killing Dracula there, his regeneration cycle ends. I really like the idea of adventuring outside the castle, so I would make this second world huge filled with various levels like forests, caves, mountains, oceans, ruins, in the clouds, etc.